NPASS Compound

Structure

CID3032 OpenBabel06191715322D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.9124 4.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5402 3.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1712 3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 30 2 0 0 0 0 17 31 2 0 0 0 0 18 32 2 0 0 0 0 18 34 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 6 0 0 0 20 25 1 0 0 0 0 20 33 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 29 1 1 0 0 0 24 34 1 0 0 0 0 25 17 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.33
Volume:	511.956
LogP:	3.477
LogD:	3.348
LogS:	-4.284
# Rotatable Bonds:	5
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	5.148
Fsp3:	0.897
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	1.7032800315064378e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.952
Plasma Protein Binding (PPB):	56.39299011230469%
Volume Distribution (VD):	1.055
Pgp-substrate:	35.86273956298828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.778
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	13.487
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.229
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.517
Skin Sensitization:	0.882
Carcinogencity:	0.274
Eye Corrosion:	0.778
Eye Irritation:	0.023
Respiratory Toxicity:	0.98

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC3032

Natural Product ID:	NPC3032
*Common Name:**	12Alpha-Acetoxy-16Beta-Hydroxy-20,24-Dimethyl-24-Oxoscalaran-25-Al
IUPAC Name:	[(1S,4aS,4bR,6S,6aS,7S,8S,9S,10aS,10bR,12aS)-8-acetyl-1-ethyl-7-formyl-9-hydroxy-1,4a,6a,10b-tetramethyl-2,3,4,4b,5,6,7,8,9,10,10a,11,12,12a-tetradecahydrochrysen-6-yl] acetate
Synonyms:
Standard InCHIKey:	WVRSKIZLQKFGLC-WJGOXMNSSA-N
Standard InCHI:	InChI=1S/C29H46O5/c1-8-26(4)11-9-12-27(5)21(26)10-13-28(6)22(27)15-24(34-18(3)32)29(7)19(16-30)25(17(2)31)20(33)14-23(28)29/h16,19-25,33H,8-15H2,1-7H3/t19-,20-,21-,22+,23-,24-,25-,26-,27-,28+,29+/m0/s1
SMILES:	O=C[C@H]1[C@H](C(=O)C)[C@@H](O)C[C@@H]2[C@]1(C)[C@@H](OC(=O)C)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465656
PubChem CID:	11102826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33404	phyllospongia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12502324]
NPO7020	Strepsichordaia lendenfeldi	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1431942]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	Niphates recondita	Weizhou Island, Beibuwan Bay, Guangxi,China	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28530828]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31265296]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32966070]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514013]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7020	Strepsichordaia lendenfeldi	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	30.0	%	PMID[554255]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[554256]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[554256]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC3032 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	3357
0.2-0.3	8572
0.3-0.4	14191
0.4-0.5	6954
0.5-0.6	5183
0.6-0.7	3009
0.7-0.8	882
0.8-0.85	33
0.85-0.9	4
0.9-0.95	5
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473319
1.0	High Similarity	NPC131104
0.9762	High Similarity	NPC475211
0.9762	High Similarity	NPC88337
0.9512	High Similarity	NPC9060
0.9512	High Similarity	NPC237938
0.9512	High Similarity	NPC219535
0.9512	High Similarity	NPC181871
0.9412	High Similarity	NPC67653
0.9412	High Similarity	NPC471459
0.9398	High Similarity	NPC474572
0.9286	High Similarity	NPC83242
0.8605	High Similarity	NPC473336
0.8605	High Similarity	NPC473299
0.8605	High Similarity	NPC477434
0.8605	High Similarity	NPC471044
0.8523	High Similarity	NPC470920
0.8478	Intermediate Similarity	NPC62407
0.8478	Intermediate Similarity	NPC287354
0.8471	Intermediate Similarity	NPC476071
0.8462	Intermediate Similarity	NPC476189
0.8427	Intermediate Similarity	NPC236459
0.8409	Intermediate Similarity	NPC120395
0.8409	Intermediate Similarity	NPC248216
0.8372	Intermediate Similarity	NPC61107
0.8372	Intermediate Similarity	NPC289486
0.8313	Intermediate Similarity	NPC474020
0.8295	Intermediate Similarity	NPC62572
0.8295	Intermediate Similarity	NPC477205
0.8295	Intermediate Similarity	NPC473350
0.8276	Intermediate Similarity	NPC15091
0.8242	Intermediate Similarity	NPC185529
0.8242	Intermediate Similarity	NPC472146
0.8191	Intermediate Similarity	NPC163685
0.8161	Intermediate Similarity	NPC268040
0.8132	Intermediate Similarity	NPC200580
0.8132	Intermediate Similarity	NPC477440
0.8132	Intermediate Similarity	NPC477443
0.8132	Intermediate Similarity	NPC61688
0.8118	Intermediate Similarity	NPC31031
0.8118	Intermediate Similarity	NPC472608
0.8118	Intermediate Similarity	NPC243594
0.8095	Intermediate Similarity	NPC108840
0.809	Intermediate Similarity	NPC131350
0.8085	Intermediate Similarity	NPC82633
0.8061	Intermediate Similarity	NPC282233
0.8061	Intermediate Similarity	NPC95585
0.8046	Intermediate Similarity	NPC50658
0.8046	Intermediate Similarity	NPC48756
0.8046	Intermediate Similarity	NPC280781
0.8046	Intermediate Similarity	NPC475743
0.8043	Intermediate Similarity	NPC477442
0.8043	Intermediate Similarity	NPC77756
0.8043	Intermediate Similarity	NPC477433
0.8043	Intermediate Similarity	NPC477444
0.8023	Intermediate Similarity	NPC201276
0.8023	Intermediate Similarity	NPC80891
0.8023	Intermediate Similarity	NPC320144
0.8021	Intermediate Similarity	NPC471038
0.8	Intermediate Similarity	NPC302111
0.8	Intermediate Similarity	NPC112463
0.8	Intermediate Similarity	NPC235109
0.8	Intermediate Similarity	NPC219353
0.8	Intermediate Similarity	NPC329910
0.7979	Intermediate Similarity	NPC469982
0.7978	Intermediate Similarity	NPC25037
0.7978	Intermediate Similarity	NPC34984
0.7976	Intermediate Similarity	NPC179858
0.7957	Intermediate Similarity	NPC52756
0.7957	Intermediate Similarity	NPC475878
0.7955	Intermediate Similarity	NPC30583
0.7931	Intermediate Similarity	NPC261616
0.7917	Intermediate Similarity	NPC472145
0.7907	Intermediate Similarity	NPC324700
0.7907	Intermediate Similarity	NPC171426
0.7907	Intermediate Similarity	NPC80089
0.7907	Intermediate Similarity	NPC185465
0.7907	Intermediate Similarity	NPC26029
0.7907	Intermediate Similarity	NPC34046
0.7907	Intermediate Similarity	NPC224802
0.7895	Intermediate Similarity	NPC470232
0.7895	Intermediate Similarity	NPC470229
0.7889	Intermediate Similarity	NPC477445
0.7882	Intermediate Similarity	NPC471046
0.7872	Intermediate Similarity	NPC199543
0.7872	Intermediate Similarity	NPC244356
0.7872	Intermediate Similarity	NPC224060
0.7857	Intermediate Similarity	NPC46848
0.7857	Intermediate Similarity	NPC52899
0.7857	Intermediate Similarity	NPC168511
0.7857	Intermediate Similarity	NPC163963
0.7857	Intermediate Similarity	NPC289148
0.7857	Intermediate Similarity	NPC159325
0.7849	Intermediate Similarity	NPC50443
0.7849	Intermediate Similarity	NPC18536
0.7835	Intermediate Similarity	NPC472144
0.7826	Intermediate Similarity	NPC477614
0.7826	Intermediate Similarity	NPC471221
0.7826	Intermediate Similarity	NPC226491
0.7812	Intermediate Similarity	NPC29410
0.7812	Intermediate Similarity	NPC193785
0.7812	Intermediate Similarity	NPC200054
0.78	Intermediate Similarity	NPC98603
0.7791	Intermediate Similarity	NPC221420
0.7791	Intermediate Similarity	NPC143133
0.7791	Intermediate Similarity	NPC298168
0.7789	Intermediate Similarity	NPC475118
0.7789	Intermediate Similarity	NPC309127
0.7789	Intermediate Similarity	NPC470385
0.7789	Intermediate Similarity	NPC470386
0.7789	Intermediate Similarity	NPC247877
0.7789	Intermediate Similarity	NPC47853
0.7778	Intermediate Similarity	NPC214946
0.7778	Intermediate Similarity	NPC319909
0.7778	Intermediate Similarity	NPC148628
0.7778	Intermediate Similarity	NPC304832
0.7778	Intermediate Similarity	NPC275990
0.7778	Intermediate Similarity	NPC470172
0.7778	Intermediate Similarity	NPC246736
0.7778	Intermediate Similarity	NPC50438
0.7778	Intermediate Similarity	NPC475689
0.7778	Intermediate Similarity	NPC88203
0.7778	Intermediate Similarity	NPC76866
0.7778	Intermediate Similarity	NPC286519
0.7766	Intermediate Similarity	NPC198054
0.7765	Intermediate Similarity	NPC159789
0.7755	Intermediate Similarity	NPC293866
0.7755	Intermediate Similarity	NPC287676
0.7755	Intermediate Similarity	NPC293890
0.7742	Intermediate Similarity	NPC56962
0.7742	Intermediate Similarity	NPC24705
0.7738	Intermediate Similarity	NPC477229
0.7738	Intermediate Similarity	NPC68426
0.7738	Intermediate Similarity	NPC282905
0.7727	Intermediate Similarity	NPC125366
0.7727	Intermediate Similarity	NPC477851
0.7717	Intermediate Similarity	NPC252714
0.7717	Intermediate Similarity	NPC239938
0.7708	Intermediate Similarity	NPC98639
0.7701	Intermediate Similarity	NPC475725
0.77	Intermediate Similarity	NPC216114
0.77	Intermediate Similarity	NPC473406
0.77	Intermediate Similarity	NPC139347
0.77	Intermediate Similarity	NPC209298
0.77	Intermediate Similarity	NPC277074
0.77	Intermediate Similarity	NPC122811
0.77	Intermediate Similarity	NPC87927
0.77	Intermediate Similarity	NPC96217
0.7684	Intermediate Similarity	NPC472147
0.7684	Intermediate Similarity	NPC474379
0.7684	Intermediate Similarity	NPC472148
0.7684	Intermediate Similarity	NPC161035
0.7677	Intermediate Similarity	NPC148279
0.7674	Intermediate Similarity	NPC472486
0.7674	Intermediate Similarity	NPC472487
0.7674	Intermediate Similarity	NPC5767
0.7674	Intermediate Similarity	NPC4209
0.7674	Intermediate Similarity	NPC475742
0.767	Intermediate Similarity	NPC87393
0.7667	Intermediate Similarity	NPC269684
0.766	Intermediate Similarity	NPC470114
0.766	Intermediate Similarity	NPC169933
0.766	Intermediate Similarity	NPC476296
0.7653	Intermediate Similarity	NPC474793
0.7653	Intermediate Similarity	NPC98837
0.7653	Intermediate Similarity	NPC26270
0.7653	Intermediate Similarity	NPC16911
0.7653	Intermediate Similarity	NPC475876
0.7653	Intermediate Similarity	NPC38296
0.7653	Intermediate Similarity	NPC78427
0.7653	Intermediate Similarity	NPC89099
0.7653	Intermediate Similarity	NPC162459
0.7653	Intermediate Similarity	NPC38471
0.7653	Intermediate Similarity	NPC20479
0.7653	Intermediate Similarity	NPC28864
0.7647	Intermediate Similarity	NPC176949
0.7647	Intermediate Similarity	NPC201908
0.7647	Intermediate Similarity	NPC55508
0.7647	Intermediate Similarity	NPC471246
0.764	Intermediate Similarity	NPC58631
0.764	Intermediate Similarity	NPC73515
0.764	Intermediate Similarity	NPC474870
0.764	Intermediate Similarity	NPC271572
0.7634	Intermediate Similarity	NPC476379
0.7634	Intermediate Similarity	NPC476435
0.7629	Intermediate Similarity	NPC475765
0.7629	Intermediate Similarity	NPC223169
0.7629	Intermediate Similarity	NPC477264
0.7629	Intermediate Similarity	NPC116683
0.7629	Intermediate Similarity	NPC475785
0.7629	Intermediate Similarity	NPC470387
0.7624	Intermediate Similarity	NPC327093
0.7624	Intermediate Similarity	NPC84928
0.7619	Intermediate Similarity	NPC157571
0.7614	Intermediate Similarity	NPC220379
0.7614	Intermediate Similarity	NPC73013
0.7609	Intermediate Similarity	NPC80700
0.7609	Intermediate Similarity	NPC476717
0.7609	Intermediate Similarity	NPC472272
0.7609	Intermediate Similarity	NPC477441

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC3032 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	555
0.1-0.2	3557
0.2-0.3	3255
0.3-0.4	1138
0.4-0.5	320
0.5-0.6	254
0.6-0.7	53
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7907	Intermediate Similarity	NPD6114	Approved
0.7907	Intermediate Similarity	NPD6115	Approved
0.7907	Intermediate Similarity	NPD6697	Approved
0.7907	Intermediate Similarity	NPD6118	Approved
0.7765	Intermediate Similarity	NPD3703	Phase 2
0.7674	Intermediate Similarity	NPD6117	Approved
0.7586	Intermediate Similarity	NPD6116	Phase 1
0.7442	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8035	Phase 2
0.7396	Intermediate Similarity	NPD8034	Phase 2
0.7238	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7902	Approved
0.7176	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7748	Approved
0.7041	Intermediate Similarity	NPD7515	Phase 2
0.7027	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5777	Approved
0.69	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD4244	Approved
0.6897	Remote Similarity	NPD4245	Approved
0.6852	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4224	Phase 2
0.6818	Remote Similarity	NPD6081	Approved
0.681	Remote Similarity	NPD8328	Phase 3
0.6792	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3698	Phase 2
0.6778	Remote Similarity	NPD3702	Approved
0.6705	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6602	Remote Similarity	NPD4697	Phase 3
0.6571	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7639	Approved
0.6559	Remote Similarity	NPD3671	Phase 1
0.6545	Remote Similarity	NPD6372	Approved
0.6545	Remote Similarity	NPD6373	Approved
0.6512	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1700	Approved
0.6496	Remote Similarity	NPD6921	Approved
0.6449	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD6675	Approved
0.6422	Remote Similarity	NPD7128	Approved
0.6422	Remote Similarity	NPD6402	Approved
0.6422	Remote Similarity	NPD5739	Approved
0.6421	Remote Similarity	NPD6928	Phase 2
0.6415	Remote Similarity	NPD8418	Phase 2
0.6393	Remote Similarity	NPD7319	Approved
0.6392	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3669	Approved
0.6383	Remote Similarity	NPD4238	Approved
0.6383	Remote Similarity	NPD4802	Phase 2
0.6373	Remote Similarity	NPD6411	Approved
0.6354	Remote Similarity	NPD1780	Approved
0.6354	Remote Similarity	NPD1779	Approved
0.6337	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD7736	Approved
0.6306	Remote Similarity	NPD7320	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6281	Remote Similarity	NPD7507	Approved
0.6273	Remote Similarity	NPD6008	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6264	Remote Similarity	NPD4758	Discontinued
0.6222	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD5701	Approved
0.6214	Remote Similarity	NPD6079	Approved
0.6211	Remote Similarity	NPD5364	Discontinued
0.62	Remote Similarity	NPD3618	Phase 1
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8133	Approved
0.6174	Remote Similarity	NPD4632	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD7115	Discovery
0.6154	Remote Similarity	NPD5779	Approved
0.6148	Remote Similarity	NPD6616	Approved
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3573	Approved
0.6134	Remote Similarity	NPD6059	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6111	Remote Similarity	NPD229	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7078	Approved
0.6098	Remote Similarity	NPD8293	Discontinued
0.6098	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6078	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6940	Discontinued
0.6033	Remote Similarity	NPD6370	Approved
0.6023	Remote Similarity	NPD7909	Approved
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD4786	Approved
0.5984	Remote Similarity	NPD7604	Phase 2
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5222	Approved
0.5979	Remote Similarity	NPD7645	Phase 2
0.596	Remote Similarity	NPD3667	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.5932	Remote Similarity	NPD6868	Approved
0.5929	Remote Similarity	NPD6412	Phase 2
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6084	Phase 2
0.5926	Remote Similarity	NPD5173	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5926	Remote Similarity	NPD6083	Phase 2
0.5913	Remote Similarity	NPD4634	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.59	Remote Similarity	NPD4788	Approved
0.5887	Remote Similarity	NPD6336	Discontinued
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5872	Remote Similarity	NPD4225	Approved
0.5865	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD8171	Discontinued
0.5841	Remote Similarity	NPD6920	Discontinued
0.5833	Remote Similarity	NPD6335	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD4700	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.5806	Remote Similarity	NPD4787	Phase 1
0.58	Remote Similarity	NPD7345	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5794	Remote Similarity	NPD6033	Approved
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.5778	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5737	Approved
0.5769	Remote Similarity	NPD6903	Approved
0.5769	Remote Similarity	NPD6672	Approved
0.5766	Remote Similarity	NPD5223	Approved
0.5763	Remote Similarity	NPD8298	Phase 2
0.575	Remote Similarity	NPD6317	Approved
0.5747	Remote Similarity	NPD3198	Approved
0.5741	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6686	Approved
0.5728	Remote Similarity	NPD5786	Approved
0.5727	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD8086	Approved
0.5714	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD8084	Approved
0.5714	Remote Similarity	NPD8138	Approved
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD8083	Approved
0.5702	Remote Similarity	NPD6314	Approved
0.5702	Remote Similarity	NPD8393	Approved
0.5702	Remote Similarity	NPD6313	Approved
0.5701	Remote Similarity	NPD4202	Approved
0.5691	Remote Similarity	NPD6909	Approved
0.5691	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6908	Approved
0.5688	Remote Similarity	NPD7614	Phase 1
0.5686	Remote Similarity	NPD3666	Approved
0.5686	Remote Similarity	NPD3133	Approved
0.5686	Remote Similarity	NPD3665	Phase 1
0.5664	Remote Similarity	NPD8276	Approved
0.5664	Remote Similarity	NPD5174	Approved
0.5664	Remote Similarity	NPD4754	Approved
0.5664	Remote Similarity	NPD8275	Approved
0.5664	Remote Similarity	NPD5175	Approved
0.5638	Remote Similarity	NPD7532	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data