NPASS Compound

Structure

NPC307258 OpenBabel07101718192D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.5731 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 -1.8827 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 -0.5000 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 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 0.8660 -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 -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 1.7321 2.0000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 1.5000 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 22 1 0 0 0 0 2 22 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 7 20 1 0 0 0 0 8 13 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 26 2 0 0 0 0 15 18 1 0 0 0 0 15 27 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 18 23 1 1 0 0 0 19 22 1 0 0 0 0 19 25 1 1 0 0 0 20 23 1 1 0 0 0 20 24 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.28
Volume:	425.192
LogP:	4.328
LogD:	3.822
LogS:	-3.938
# Rotatable Bonds:	3
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	4.874
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.721
MDCK Permeability:	1.6142528693308122e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.656
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.904
Plasma Protein Binding (PPB):	54.872474670410156%
Volume Distribution (VD):	2.458
Pgp-substrate:	32.08149719238281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	10.103
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.461
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.521
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.969
Carcinogencity:	0.735
Eye Corrosion:	0.972
Eye Irritation:	0.897
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC307258

Natural Product ID:	NPC307258
*Common Name:**	12-Deacetoxy-23-Hydroxyscalaradial
IUPAC Name:	(1R,4aS,4bS,6aS,10aR,10bS,12aS)-10a-(hydroxymethyl)-4b,7,7,12a-tetramethyl-1,4,4a,5,6,6a,8,9,10,10b,11,12-dodecahydrochrysene-1,2-dicarbaldehyde
Synonyms:
Standard InCHIKey:	BERUNAPIPIALIL-CTBGZIJUSA-N
Standard InCHI:	InChI=1S/C25H38O3/c1-22(2)10-5-11-25(16-28)19(22)8-13-24(4)20-7-6-17(14-26)18(15-27)23(20,3)12-9-21(24)25/h6,14-15,18-21,28H,5,7-13,16H2,1-4H3/t18-,19-,20+,21-,23+,24-,25+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(CO)[C@H]1CC[C@@]1(C)[C@@H]3CC=C(C=O)[C@H](C=O)[C@@]3(C)CC[C@H]21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2348186
PubChem CID:	71579675
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
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270579]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	Korean	n.a.	PMID[23489626]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621941]

☑ 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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3885	Cell Line	CV-1	Chlorocebus aethiops	IC50	>	50000.0	nM	PMID[551577]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[551577]
NPT376	Cell Line	A498	Homo sapiens	IC50	>	50000.0	nM	PMID[551577]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	34300.0	nM	PMID[551577]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31100.0	nM	PMID[551577]

☑ 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 NPC307258 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	177
0.1-0.2	1361
0.2-0.3	6159
0.3-0.4	15675
0.4-0.5	8081
0.5-0.6	5966
0.6-0.7	3949
0.7-0.8	1197
0.8-0.85	109
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC184663
0.9157	High Similarity	NPC206060
0.8929	High Similarity	NPC474925
0.8875	High Similarity	NPC2482
0.8837	High Similarity	NPC230064
0.8831	High Similarity	NPC211641
0.8824	High Similarity	NPC477973
0.881	High Similarity	NPC93778
0.8765	High Similarity	NPC3915
0.8736	High Similarity	NPC151722
0.869	High Similarity	NPC477579
0.869	High Similarity	NPC235341
0.869	High Similarity	NPC95594
0.8659	High Similarity	NPC310989
0.8652	High Similarity	NPC5532
0.8652	High Similarity	NPC61369
0.8652	High Similarity	NPC469545
0.8625	High Similarity	NPC59436
0.859	High Similarity	NPC128346
0.859	High Similarity	NPC219232
0.8571	High Similarity	NPC2709
0.8537	High Similarity	NPC471898
0.8537	High Similarity	NPC121984
0.8506	High Similarity	NPC85173
0.85	High Similarity	NPC471897
0.85	High Similarity	NPC107039
0.85	High Similarity	NPC471899
0.8488	Intermediate Similarity	NPC472802
0.8471	Intermediate Similarity	NPC158393
0.8452	Intermediate Similarity	NPC470812
0.8452	Intermediate Similarity	NPC214043
0.8452	Intermediate Similarity	NPC85774
0.8452	Intermediate Similarity	NPC180834
0.8452	Intermediate Similarity	NPC476412
0.8415	Intermediate Similarity	NPC472478
0.8415	Intermediate Similarity	NPC104545
0.8409	Intermediate Similarity	NPC272746
0.8395	Intermediate Similarity	NPC280654
0.8395	Intermediate Similarity	NPC115515
0.8395	Intermediate Similarity	NPC110094
0.8395	Intermediate Similarity	NPC260385
0.8391	Intermediate Similarity	NPC469546
0.8375	Intermediate Similarity	NPC89294
0.8353	Intermediate Similarity	NPC133954
0.8353	Intermediate Similarity	NPC474537
0.8353	Intermediate Similarity	NPC274724
0.8353	Intermediate Similarity	NPC469948
0.8333	Intermediate Similarity	NPC53733
0.8333	Intermediate Similarity	NPC175410
0.8313	Intermediate Similarity	NPC278459
0.8313	Intermediate Similarity	NPC116797
0.8313	Intermediate Similarity	NPC90055
0.8313	Intermediate Similarity	NPC473217
0.8295	Intermediate Similarity	NPC159748
0.8295	Intermediate Similarity	NPC101651
0.8295	Intermediate Similarity	NPC191684
0.8293	Intermediate Similarity	NPC231431
0.8293	Intermediate Similarity	NPC16394
0.8293	Intermediate Similarity	NPC199595
0.8276	Intermediate Similarity	NPC474474
0.8261	Intermediate Similarity	NPC194196
0.8256	Intermediate Similarity	NPC145879
0.8256	Intermediate Similarity	NPC31564
0.8256	Intermediate Similarity	NPC474733
0.8256	Intermediate Similarity	NPC475862
0.8256	Intermediate Similarity	NPC324063
0.8256	Intermediate Similarity	NPC474732
0.8256	Intermediate Similarity	NPC474778
0.8256	Intermediate Similarity	NPC74363
0.8256	Intermediate Similarity	NPC213412
0.8235	Intermediate Similarity	NPC329043
0.8235	Intermediate Similarity	NPC473246
0.8235	Intermediate Similarity	NPC237712
0.8235	Intermediate Similarity	NPC58841
0.8235	Intermediate Similarity	NPC321187
0.8235	Intermediate Similarity	NPC161423
0.8235	Intermediate Similarity	NPC227064
0.8235	Intermediate Similarity	NPC96095
0.8222	Intermediate Similarity	NPC471207
0.8222	Intermediate Similarity	NPC23170
0.8214	Intermediate Similarity	NPC142683
0.8214	Intermediate Similarity	NPC103486
0.8202	Intermediate Similarity	NPC158030
0.8202	Intermediate Similarity	NPC65120
0.8202	Intermediate Similarity	NPC4036
0.8202	Intermediate Similarity	NPC233455
0.8202	Intermediate Similarity	NPC145067
0.8193	Intermediate Similarity	NPC477057
0.8193	Intermediate Similarity	NPC476809
0.8193	Intermediate Similarity	NPC37038
0.8182	Intermediate Similarity	NPC472983
0.8171	Intermediate Similarity	NPC80088
0.8171	Intermediate Similarity	NPC253561
0.8171	Intermediate Similarity	NPC62336
0.8161	Intermediate Similarity	NPC98442
0.8161	Intermediate Similarity	NPC171203
0.8161	Intermediate Similarity	NPC475740
0.8161	Intermediate Similarity	NPC158141
0.8161	Intermediate Similarity	NPC307426
0.8161	Intermediate Similarity	NPC68160
0.8161	Intermediate Similarity	NPC242468
0.8161	Intermediate Similarity	NPC130577
0.8161	Intermediate Similarity	NPC73064
0.8161	Intermediate Similarity	NPC142415
0.8161	Intermediate Similarity	NPC88716
0.8161	Intermediate Similarity	NPC173089
0.8161	Intermediate Similarity	NPC293564
0.8161	Intermediate Similarity	NPC51700
0.8161	Intermediate Similarity	NPC102683
0.8161	Intermediate Similarity	NPC71507
0.8161	Intermediate Similarity	NPC470523
0.8161	Intermediate Similarity	NPC58063
0.8161	Intermediate Similarity	NPC18064
0.8148	Intermediate Similarity	NPC470525
0.8148	Intermediate Similarity	NPC263582
0.814	Intermediate Similarity	NPC470574
0.814	Intermediate Similarity	NPC476426
0.814	Intermediate Similarity	NPC469993
0.8118	Intermediate Similarity	NPC200752
0.8118	Intermediate Similarity	NPC470165
0.8111	Intermediate Similarity	NPC295643
0.8111	Intermediate Similarity	NPC250575
0.8111	Intermediate Similarity	NPC272075
0.8111	Intermediate Similarity	NPC298554
0.8111	Intermediate Similarity	NPC214756
0.8105	Intermediate Similarity	NPC95585
0.8105	Intermediate Similarity	NPC282233
0.8095	Intermediate Similarity	NPC267691
0.8095	Intermediate Similarity	NPC263272
0.8095	Intermediate Similarity	NPC274050
0.8095	Intermediate Similarity	NPC142244
0.8095	Intermediate Similarity	NPC162632
0.8095	Intermediate Similarity	NPC221647
0.809	Intermediate Similarity	NPC328141
0.809	Intermediate Similarity	NPC126993
0.8072	Intermediate Similarity	NPC474113
0.8072	Intermediate Similarity	NPC152061
0.8072	Intermediate Similarity	NPC472490
0.8068	Intermediate Similarity	NPC470629
0.8068	Intermediate Similarity	NPC181225
0.8068	Intermediate Similarity	NPC290690
0.8068	Intermediate Similarity	NPC474512
0.8068	Intermediate Similarity	NPC182797
0.8068	Intermediate Similarity	NPC470524
0.8068	Intermediate Similarity	NPC40552
0.8068	Intermediate Similarity	NPC246708
0.8068	Intermediate Similarity	NPC1753
0.8068	Intermediate Similarity	NPC473229
0.8068	Intermediate Similarity	NPC17733
0.8068	Intermediate Similarity	NPC474511
0.8068	Intermediate Similarity	NPC52169
0.8068	Intermediate Similarity	NPC473242
0.8065	Intermediate Similarity	NPC471966
0.8052	Intermediate Similarity	NPC290350
0.8052	Intermediate Similarity	NPC4370
0.8049	Intermediate Similarity	NPC165711
0.8049	Intermediate Similarity	NPC149249
0.8049	Intermediate Similarity	NPC197659
0.8049	Intermediate Similarity	NPC106078
0.8049	Intermediate Similarity	NPC470428
0.8046	Intermediate Similarity	NPC327115
0.8046	Intermediate Similarity	NPC269396
0.8046	Intermediate Similarity	NPC94755
0.8046	Intermediate Similarity	NPC72638
0.8046	Intermediate Similarity	NPC94666
0.8046	Intermediate Similarity	NPC98236
0.8043	Intermediate Similarity	NPC473158
0.8043	Intermediate Similarity	NPC471039
0.8025	Intermediate Similarity	NPC279666
0.8025	Intermediate Similarity	NPC192540
0.8023	Intermediate Similarity	NPC472265
0.8023	Intermediate Similarity	NPC227132
0.8023	Intermediate Similarity	NPC59453
0.8023	Intermediate Similarity	NPC82902
0.8023	Intermediate Similarity	NPC221758
0.8022	Intermediate Similarity	NPC269729
0.8022	Intermediate Similarity	NPC222047
0.8022	Intermediate Similarity	NPC209868
0.8	Intermediate Similarity	NPC151519
0.8	Intermediate Similarity	NPC212083
0.8	Intermediate Similarity	NPC251779
0.8	Intermediate Similarity	NPC476187
0.8	Intermediate Similarity	NPC69101
0.8	Intermediate Similarity	NPC48362
0.8	Intermediate Similarity	NPC470813
0.7978	Intermediate Similarity	NPC69627
0.7978	Intermediate Similarity	NPC186688
0.7978	Intermediate Similarity	NPC26959
0.7978	Intermediate Similarity	NPC234346
0.7978	Intermediate Similarity	NPC64872
0.7978	Intermediate Similarity	NPC130520
0.7978	Intermediate Similarity	NPC121798
0.7978	Intermediate Similarity	NPC263393
0.7978	Intermediate Similarity	NPC225585
0.7978	Intermediate Similarity	NPC95246
0.7978	Intermediate Similarity	NPC274330
0.7978	Intermediate Similarity	NPC474972
0.7978	Intermediate Similarity	NPC31985
0.7978	Intermediate Similarity	NPC470588
0.7978	Intermediate Similarity	NPC477943

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 NPC307258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1739
0.2-0.3	4042
0.3-0.4	2281
0.4-0.5	518
0.5-0.6	170
0.6-0.7	170
0.7-0.8	62
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD3133	Approved
0.8235	Intermediate Similarity	NPD3665	Phase 1
0.8235	Intermediate Similarity	NPD3666	Approved
0.8202	Intermediate Similarity	NPD7515	Phase 2
0.8046	Intermediate Similarity	NPD3618	Phase 1
0.8023	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7978	Intermediate Similarity	NPD5328	Approved
0.7976	Intermediate Similarity	NPD4695	Discontinued
0.7849	Intermediate Similarity	NPD4697	Phase 3
0.7826	Intermediate Similarity	NPD7748	Approved
0.7791	Intermediate Similarity	NPD4221	Approved
0.7791	Intermediate Similarity	NPD4223	Phase 3
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.7766	Intermediate Similarity	NPD7902	Approved
0.7727	Intermediate Similarity	NPD5329	Approved
0.7701	Intermediate Similarity	NPD4788	Approved
0.7667	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5279	Phase 3
0.7614	Intermediate Similarity	NPD4197	Approved
0.7582	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4629	Approved
0.7553	Intermediate Similarity	NPD5210	Approved
0.7529	Intermediate Similarity	NPD3617	Approved
0.7527	Intermediate Similarity	NPD4202	Approved
0.7474	Intermediate Similarity	NPD5221	Approved
0.7474	Intermediate Similarity	NPD5222	Approved
0.7474	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7900	Approved
0.7447	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6684	Approved
0.7444	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD4690	Approved
0.7444	Intermediate Similarity	NPD5205	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7444	Intermediate Similarity	NPD7334	Approved
0.7444	Intermediate Similarity	NPD7521	Approved
0.7444	Intermediate Similarity	NPD4688	Approved
0.7444	Intermediate Similarity	NPD7146	Approved
0.7444	Intermediate Similarity	NPD6409	Approved
0.7444	Intermediate Similarity	NPD4138	Approved
0.7444	Intermediate Similarity	NPD5330	Approved
0.7444	Intermediate Similarity	NPD4693	Phase 3
0.7444	Intermediate Similarity	NPD4689	Approved
0.7444	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5690	Phase 2
0.7442	Intermediate Similarity	NPD7645	Phase 2
0.7396	Intermediate Similarity	NPD6084	Phase 2
0.7396	Intermediate Similarity	NPD6083	Phase 2
0.7396	Intermediate Similarity	NPD5173	Approved
0.734	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD7614	Phase 1
0.7283	Intermediate Similarity	NPD6903	Approved
0.7283	Intermediate Similarity	NPD6672	Approved
0.7283	Intermediate Similarity	NPD5737	Approved
0.7253	Intermediate Similarity	NPD4694	Approved
0.7253	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7241	Intermediate Similarity	NPD4195	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD4755	Approved
0.7195	Intermediate Similarity	NPD4137	Phase 3
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD7339	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7108	Intermediate Similarity	NPD4747	Approved
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4700	Approved
0.7059	Intermediate Similarity	NPD4058	Approved
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.701	Intermediate Similarity	NPD5695	Phase 3
0.699	Remote Similarity	NPD6412	Phase 2
0.697	Remote Similarity	NPD5696	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD7525	Registered
0.6961	Remote Similarity	NPD5141	Approved
0.6939	Remote Similarity	NPD7732	Phase 3
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6893	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD7128	Approved
0.6893	Remote Similarity	NPD6675	Approved
0.6893	Remote Similarity	NPD6402	Approved
0.6889	Remote Similarity	NPD8028	Phase 2
0.6887	Remote Similarity	NPD6649	Approved
0.6887	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6875	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD4754	Approved
0.686	Remote Similarity	NPD5733	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD6673	Approved
0.6842	Remote Similarity	NPD6080	Approved
0.6842	Remote Similarity	NPD6904	Approved
0.6829	Remote Similarity	NPD7331	Phase 2
0.6827	Remote Similarity	NPD5697	Approved
0.6824	Remote Similarity	NPD4243	Approved
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6771	Remote Similarity	NPD4096	Approved
0.6762	Remote Similarity	NPD7320	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD5168	Approved
0.6762	Remote Similarity	NPD6011	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6737	Remote Similarity	NPD5208	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6731	Remote Similarity	NPD4767	Approved
0.6731	Remote Similarity	NPD4768	Approved
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6707	Remote Similarity	NPD7341	Phase 2
0.6706	Remote Similarity	NPD4244	Approved
0.6706	Remote Similarity	NPD4245	Approved
0.6706	Remote Similarity	NPD4789	Approved
0.6703	Remote Similarity	NPD4139	Approved
0.6703	Remote Similarity	NPD4692	Approved
0.6702	Remote Similarity	NPD6098	Approved
0.6701	Remote Similarity	NPD6411	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5133	Approved
0.6628	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5276	Approved
0.6628	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6686	Approved
0.6602	Remote Similarity	NPD5091	Approved
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3698	Phase 2
0.6577	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD5217	Approved
0.6574	Remote Similarity	NPD5216	Approved
0.6574	Remote Similarity	NPD5127	Approved
0.6562	Remote Similarity	NPD4518	Approved
0.6531	Remote Similarity	NPD6050	Approved
0.6531	Remote Similarity	NPD5693	Phase 1
0.6517	Remote Similarity	NPD6933	Approved
0.6506	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6101	Approved
0.6486	Remote Similarity	NPD6868	Approved
0.6477	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5290	Discontinued
0.6455	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD5692	Phase 3
0.6421	Remote Similarity	NPD1696	Phase 3
0.6421	Remote Similarity	NPD1694	Approved
0.6404	Remote Similarity	NPD5275	Approved
0.6404	Remote Similarity	NPD4190	Phase 3
0.64	Remote Similarity	NPD6001	Approved
0.6396	Remote Similarity	NPD5167	Approved
0.6395	Remote Similarity	NPD6923	Approved
0.6395	Remote Similarity	NPD6922	Approved

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