NPASS Compound

Structure

CID127798 OpenBabel06191715482D 32 36 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 3.8660 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 -2.0000 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 -3.4641 -2.0000 0.0000 C 0 0 1 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 -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 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 3.0000 0.0000 C 0 0 0 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 31 2 0 0 0 0 21 24 1 0 0 0 0 21 32 2 0 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 23 26 1 6 0 0 0 23 29 1 0 0 0 0 24 27 1 1 0 0 0 24 30 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	5.749
LogD:	5.333
LogS:	-6.244
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	4.93
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.299
MDCK Permeability:	9.689990292827133e-06
Pgp-inhibitor:	0.665
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	95.16773223876953%
Volume Distribution (VD):	1.358
Pgp-substrate:	2.3706343173980713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.959
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.189
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.408
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.547

ADMET: Excretion

Clearance (CL):	11.316
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.139
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.214
Skin Sensitization:	0.095
Carcinogencity:	0.019
Eye Corrosion:	0.041
Eye Irritation:	0.057
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC127798

Natural Product ID:	NPC127798
*Common Name:**	Putranjivadione
IUPAC Name:	(4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bR)-4,4a,6a,6b,8a,11,11,14a-octamethyl-1,2,4,5,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydropicene-3,6-dione
Synonyms:	Putranjivadione
Standard InCHIKey:	GPIWSGIAALYKPX-CITAGXGHSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19-20(31)9-10-22-27(5)14-16-29(7)23-18-25(2,3)11-12-26(23,4)13-15-30(29,8)24(27)21(32)17-28(19,22)6/h19,22-24H,9-18H2,1-8H3/t19-,22-,23+,24-,26+,27-,28+,29-,30+/m0/s1
SMILES:	O=C1C[C@]2(C)[C@@H](C)C(=O)CC[C@H]2[C@]2([C@H]1[C@@]1(C)CC[C@@]3([C@H]([C@@]1(CC2)C)CC(CC3)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460550
PubChem CID:	21596176
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12713415]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32941036]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17883	Salvia infuscata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20429	Porophyllum riedelii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21042	Penstemon richardsonii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22642	Ardisia virens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22135	Dahlia scapigera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22013	Epithelantha micromeris	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21744	Aldisa smaragdina	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23501	Symphytum asperum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24294	Lolium cuneatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27914	Osteospermum imbricatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23060	Hedeoma pulegioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23415	Dalea tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[490214]
NPT407	Cell Line	COLO 205	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[490214]

☑ 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 NPC127798 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	677
0.1-0.2	10777
0.2-0.3	17303
0.3-0.4	6910
0.4-0.5	4916
0.5-0.6	1823
0.6-0.7	238
0.7-0.8	39
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC307063
0.8276	Intermediate Similarity	NPC143597
0.8276	Intermediate Similarity	NPC151464
0.8246	Intermediate Similarity	NPC288296
0.8246	Intermediate Similarity	NPC53245
0.8182	Intermediate Similarity	NPC290058
0.8103	Intermediate Similarity	NPC184819
0.8	Intermediate Similarity	NPC475977
0.8	Intermediate Similarity	NPC2568
0.8	Intermediate Similarity	NPC281203
0.8	Intermediate Similarity	NPC103647
0.8	Intermediate Similarity	NPC180777
0.8	Intermediate Similarity	NPC469724
0.8	Intermediate Similarity	NPC100917
0.8	Intermediate Similarity	NPC31187
0.8	Intermediate Similarity	NPC260319
0.7794	Intermediate Similarity	NPC474488
0.7667	Intermediate Similarity	NPC474105
0.7647	Intermediate Similarity	NPC247195
0.7612	Intermediate Similarity	NPC286814
0.7576	Intermediate Similarity	NPC20181
0.7576	Intermediate Similarity	NPC220210
0.7536	Intermediate Similarity	NPC282905
0.7536	Intermediate Similarity	NPC68426
0.7536	Intermediate Similarity	NPC475230
0.7536	Intermediate Similarity	NPC477229
0.7463	Intermediate Similarity	NPC39157
0.7463	Intermediate Similarity	NPC142754
0.7463	Intermediate Similarity	NPC82477
0.7463	Intermediate Similarity	NPC296697
0.7463	Intermediate Similarity	NPC473225
0.7429	Intermediate Similarity	NPC130011
0.7429	Intermediate Similarity	NPC168511
0.7429	Intermediate Similarity	NPC159325
0.7424	Intermediate Similarity	NPC43300
0.7391	Intermediate Similarity	NPC190035
0.7324	Intermediate Similarity	NPC267753
0.7246	Intermediate Similarity	NPC108131
0.7222	Intermediate Similarity	NPC108840
0.7206	Intermediate Similarity	NPC470956
0.7143	Intermediate Similarity	NPC225467
0.7123	Intermediate Similarity	NPC112463
0.7101	Intermediate Similarity	NPC178541
0.7042	Intermediate Similarity	NPC81759
0.7027	Intermediate Similarity	NPC26029
0.7015	Intermediate Similarity	NPC469791
0.6957	Remote Similarity	NPC474954
0.6944	Remote Similarity	NPC159497
0.6912	Remote Similarity	NPC96812
0.6912	Remote Similarity	NPC189917
0.6912	Remote Similarity	NPC107704
0.6912	Remote Similarity	NPC168824
0.6912	Remote Similarity	NPC39462
0.6901	Remote Similarity	NPC472309
0.6857	Remote Similarity	NPC477857
0.6857	Remote Similarity	NPC474962
0.6852	Remote Similarity	NPC135077
0.6852	Remote Similarity	NPC45270
0.6852	Remote Similarity	NPC59570
0.6852	Remote Similarity	NPC215118
0.6849	Remote Similarity	NPC72444
0.6849	Remote Similarity	NPC195155
0.6849	Remote Similarity	NPC97534
0.6849	Remote Similarity	NPC174964
0.6835	Remote Similarity	NPC62572
0.6833	Remote Similarity	NPC274182
0.68	Remote Similarity	NPC243594
0.68	Remote Similarity	NPC31031
0.68	Remote Similarity	NPC115515
0.68	Remote Similarity	NPC472608
0.6786	Remote Similarity	NPC171783
0.6761	Remote Similarity	NPC40574
0.6757	Remote Similarity	NPC475742
0.6757	Remote Similarity	NPC5767
0.6753	Remote Similarity	NPC50658
0.6712	Remote Similarity	NPC133922
0.6711	Remote Similarity	NPC73013
0.6667	Remote Similarity	NPC221420
0.6667	Remote Similarity	NPC23884
0.6667	Remote Similarity	NPC30583
0.6667	Remote Similarity	NPC197701
0.6667	Remote Similarity	NPC58057
0.6667	Remote Similarity	NPC320549
0.6667	Remote Similarity	NPC42060
0.6667	Remote Similarity	NPC151018
0.6667	Remote Similarity	NPC156277
0.6667	Remote Similarity	NPC223187
0.6623	Remote Similarity	NPC267517
0.6623	Remote Similarity	NPC18955
0.6622	Remote Similarity	NPC472311
0.662	Remote Similarity	NPC131892
0.662	Remote Similarity	NPC324607
0.662	Remote Similarity	NPC327728
0.662	Remote Similarity	NPC6120
0.662	Remote Similarity	NPC213178
0.662	Remote Similarity	NPC321732
0.6618	Remote Similarity	NPC469662
0.6579	Remote Similarity	NPC63020
0.6575	Remote Similarity	NPC474123
0.6575	Remote Similarity	NPC232112
0.6575	Remote Similarity	NPC36310
0.6575	Remote Similarity	NPC310766
0.6575	Remote Similarity	NPC52667
0.6567	Remote Similarity	NPC60565
0.6538	Remote Similarity	NPC274050
0.6538	Remote Similarity	NPC267691
0.6538	Remote Similarity	NPC474870
0.6538	Remote Similarity	NPC280781
0.6538	Remote Similarity	NPC476071
0.6538	Remote Similarity	NPC48756
0.6538	Remote Similarity	NPC3915
0.6538	Remote Similarity	NPC263272
0.6538	Remote Similarity	NPC271572
0.6538	Remote Similarity	NPC162632
0.6528	Remote Similarity	NPC214770
0.6528	Remote Similarity	NPC477856
0.6528	Remote Similarity	NPC476731
0.6522	Remote Similarity	NPC19311
0.6522	Remote Similarity	NPC230047
0.65	Remote Similarity	NPC293343
0.65	Remote Similarity	NPC105895
0.65	Remote Similarity	NPC247786
0.65	Remote Similarity	NPC34984
0.65	Remote Similarity	NPC25037
0.65	Remote Similarity	NPC258672
0.6494	Remote Similarity	NPC201459
0.6494	Remote Similarity	NPC192744
0.6486	Remote Similarity	NPC162164
0.6486	Remote Similarity	NPC255168
0.6486	Remote Similarity	NPC472854
0.6486	Remote Similarity	NPC254340
0.6479	Remote Similarity	NPC20610
0.6471	Remote Similarity	NPC197238
0.6471	Remote Similarity	NPC202118
0.6456	Remote Similarity	NPC163236
0.6456	Remote Similarity	NPC69101
0.6456	Remote Similarity	NPC310989
0.6456	Remote Similarity	NPC251779
0.6447	Remote Similarity	NPC298168
0.6447	Remote Similarity	NPC143133
0.6438	Remote Similarity	NPC89310
0.6438	Remote Similarity	NPC126642
0.6438	Remote Similarity	NPC473267
0.6438	Remote Similarity	NPC305501
0.6438	Remote Similarity	NPC110615
0.6429	Remote Similarity	NPC477931
0.6429	Remote Similarity	NPC323005
0.6429	Remote Similarity	NPC268736
0.641	Remote Similarity	NPC287063
0.6406	Remote Similarity	NPC200258
0.64	Remote Similarity	NPC179858
0.64	Remote Similarity	NPC255650
0.64	Remote Similarity	NPC21220
0.64	Remote Similarity	NPC293803
0.64	Remote Similarity	NPC273366
0.64	Remote Similarity	NPC125767
0.6389	Remote Similarity	NPC476734
0.6389	Remote Similarity	NPC295788
0.6389	Remote Similarity	NPC196197
0.6389	Remote Similarity	NPC319671
0.6389	Remote Similarity	NPC182815
0.6389	Remote Similarity	NPC252032
0.6389	Remote Similarity	NPC139397
0.6389	Remote Similarity	NPC469941
0.6375	Remote Similarity	NPC70834
0.6375	Remote Similarity	NPC269684
0.6364	Remote Similarity	NPC141634
0.6351	Remote Similarity	NPC177826
0.6351	Remote Similarity	NPC303613
0.6351	Remote Similarity	NPC474228
0.6338	Remote Similarity	NPC472984
0.6338	Remote Similarity	NPC130459
0.6338	Remote Similarity	NPC478180
0.6338	Remote Similarity	NPC474221
0.6338	Remote Similarity	NPC41542
0.6333	Remote Similarity	NPC294440
0.6333	Remote Similarity	NPC20017
0.6329	Remote Similarity	NPC103754
0.6329	Remote Similarity	NPC475863
0.6329	Remote Similarity	NPC474484
0.6316	Remote Similarity	NPC472486
0.6316	Remote Similarity	NPC472487
0.6316	Remote Similarity	NPC471046
0.6301	Remote Similarity	NPC159577
0.6301	Remote Similarity	NPC2634
0.6301	Remote Similarity	NPC251929
0.6301	Remote Similarity	NPC35734
0.6301	Remote Similarity	NPC307176
0.6301	Remote Similarity	NPC260040
0.6301	Remote Similarity	NPC282593
0.6301	Remote Similarity	NPC477929
0.6301	Remote Similarity	NPC265782
0.6296	Remote Similarity	NPC96095
0.6296	Remote Similarity	NPC312660
0.6296	Remote Similarity	NPC180834
0.629	Remote Similarity	NPC236623
0.6282	Remote Similarity	NPC472310
0.6282	Remote Similarity	NPC16394
0.6279	Remote Similarity	NPC472147
0.6279	Remote Similarity	NPC472148

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 NPC127798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	751
0.1-0.2	5425
0.2-0.3	2249
0.3-0.4	437
0.4-0.5	214
0.5-0.6	59
0.6-0.7	15
0.7-0.8	0
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
0.7143	Intermediate Similarity	NPD6081	Approved
0.6957	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5360	Phase 3
0.6912	Remote Similarity	NPD4224	Phase 2
0.6761	Remote Similarity	NPD4244	Approved
0.6761	Remote Similarity	NPD4789	Approved
0.6761	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3698	Phase 2
0.662	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4758	Discontinued
0.6389	Remote Similarity	NPD4137	Phase 3
0.6329	Remote Similarity	NPD8028	Phase 2
0.6301	Remote Similarity	NPD4747	Approved
0.6301	Remote Similarity	NPD4691	Approved
0.6267	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD3703	Phase 2
0.6167	Remote Similarity	NPD343	Approved
0.6167	Remote Similarity	NPD345	Approved
0.6167	Remote Similarity	NPD344	Approved
0.6154	Remote Similarity	NPD4776	Phase 2
0.6154	Remote Similarity	NPD4777	Suspended
0.6154	Remote Similarity	NPD5364	Discontinued
0.6104	Remote Similarity	NPD6117	Approved
0.6053	Remote Similarity	NPD4058	Approved
0.6053	Remote Similarity	NPD5733	Approved
0.6026	Remote Similarity	NPD6116	Phase 1
0.5949	Remote Similarity	NPD6115	Approved
0.5949	Remote Similarity	NPD6118	Approved
0.5949	Remote Similarity	NPD6114	Approved
0.5949	Remote Similarity	NPD3671	Phase 1
0.5949	Remote Similarity	NPD6697	Approved
0.5844	Remote Similarity	NPD4687	Approved
0.5833	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD7515	Phase 2
0.5789	Remote Similarity	NPD5276	Approved
0.5783	Remote Similarity	NPD4788	Approved
0.5769	Remote Similarity	NPD3702	Approved
0.575	Remote Similarity	NPD3617	Approved
0.5747	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7732	Phase 3
0.5714	Remote Similarity	NPD7614	Phase 1
0.5667	Remote Similarity	NPD7748	Approved
0.5667	Remote Similarity	NPD7900	Approved
0.5667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7513	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