NPASS Compound

Structure

NPC230888 OpenBabel07101719512D 36 40 0 0 1 0 0 0 0 0999 V2000 -9.1664 4.4680 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1883 4.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4670 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 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 -4.3301 2.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 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 -6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 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 0.8660 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 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 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 -0.0000 -0.0000 0.0000 O 0 0 0 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 3 17 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 6 19 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 30 2 0 0 0 0 16 2 1 6 0 0 0 16 26 1 0 0 0 0 16 34 1 0 0 0 0 17 31 2 0 0 0 0 17 35 1 0 0 0 0 18 28 1 6 0 0 0 19 29 1 6 0 0 0 20 36 1 6 0 0 0 21 8 1 1 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 28 1 6 0 0 0 23 29 1 6 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 6 0 0 0 25 27 1 0 0 0 0 25 33 1 1 0 0 0 26 35 1 6 0 0 0 27 34 1 0 0 0 0 27 36 1 1 0 0 0 28 4 1 6 0 0 0 29 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.31
Volume:	520.98
LogP:	3.85
LogD:	4.128
LogS:	-4.111
# Rotatable Bonds:	6
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	5.119
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.795
MDCK Permeability:	2.635017517604865e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.93
Human Intestinal Absorption (HIA):	0.269
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.864
Plasma Protein Binding (PPB):	67.0681381225586%
Volume Distribution (VD):	1.662
Pgp-substrate:	30.698745727539062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.389
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	2.108
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.686
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.654
AMES Toxicity:	0.316
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.763
Skin Sensitization:	0.979
Carcinogencity:	0.303
Eye Corrosion:	0.412
Eye Irritation:	0.584
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC230888

Natural Product ID:	NPC230888
*Common Name:**	Stereonsteroid E
IUPAC Name:	[(2S,3S,4S,5S,6R)-6-[[(3S,5S,8S,9S,10R,13R,14S,17R)-17-ethenyl-10-formyl-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:	Stereonsteroid E
Standard InCHIKey:	AIYZYMIXDUIBLQ-KFHYCKKOSA-N
Standard InCHI:	InChI=1S/C29H44O7/c1-5-18-7-9-22-21-8-6-19-14-20(10-13-29(19,15-30)23(21)11-12-28(18,22)4)36-27-25(33)24(32)26(16(2)34-27)35-17(3)31/h5,15-16,18-27,32-33H,1,6-14H2,2-4H3/t16-,18-,19-,20-,21-,22-,23-,24-,25-,26+,27-,28+,29+/m0/s1
SMILES:	C=C[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C=O)[C@H]3CC[C@]12C)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](C)O1)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509078
PubChem CID:	11562462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33076	stereonephthya crystalliana	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16441077]

☑ 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	1
IC50	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	9.3	ug ml-1	PMID[448124]
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.8	ug.mL-1	PMID[448124]

☑ 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 NPC230888 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	232
0.1-0.2	1795
0.2-0.3	5859
0.3-0.4	12788
0.4-0.5	8737
0.5-0.6	5948
0.6-0.7	4140
0.7-0.8	2830
0.8-0.85	325
0.85-0.9	36
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC278939
0.9091	High Similarity	NPC473555
0.9091	High Similarity	NPC471770
0.9	High Similarity	NPC157739
0.8922	High Similarity	NPC94919
0.8911	High Similarity	NPC317019
0.8857	High Similarity	NPC88744
0.8774	High Similarity	NPC240125
0.8774	High Similarity	NPC473844
0.8774	High Similarity	NPC91583
0.8774	High Similarity	NPC51947
0.8713	High Similarity	NPC472273
0.8679	High Similarity	NPC295389
0.8636	High Similarity	NPC137414
0.8611	High Similarity	NPC263827
0.8611	High Similarity	NPC204392
0.8611	High Similarity	NPC240734
0.8611	High Similarity	NPC275668
0.8611	High Similarity	NPC91838
0.8611	High Similarity	NPC285410
0.8611	High Similarity	NPC250481
0.8611	High Similarity	NPC11035
0.8611	High Similarity	NPC272242
0.8611	High Similarity	NPC1876
0.8586	High Similarity	NPC48463
0.8585	High Similarity	NPC287269
0.8545	High Similarity	NPC472274
0.8532	High Similarity	NPC470543
0.8532	High Similarity	NPC243572
0.8519	High Similarity	NPC129340
0.8505	High Similarity	NPC224414
0.8482	Intermediate Similarity	NPC469822
0.8455	Intermediate Similarity	NPC146563
0.8455	Intermediate Similarity	NPC102619
0.8455	Intermediate Similarity	NPC73986
0.8448	Intermediate Similarity	NPC250556
0.8448	Intermediate Similarity	NPC469750
0.8426	Intermediate Similarity	NPC118225
0.8426	Intermediate Similarity	NPC265655
0.8426	Intermediate Similarity	NPC8431
0.8393	Intermediate Similarity	NPC473304
0.8381	Intermediate Similarity	NPC154452
0.8378	Intermediate Similarity	NPC54395
0.8378	Intermediate Similarity	NPC469821
0.8376	Intermediate Similarity	NPC471356
0.8376	Intermediate Similarity	NPC179412
0.8364	Intermediate Similarity	NPC471245
0.8349	Intermediate Similarity	NPC106760
0.8349	Intermediate Similarity	NPC101450
0.8333	Intermediate Similarity	NPC195708
0.8333	Intermediate Similarity	NPC63841
0.8319	Intermediate Similarity	NPC239293
0.8318	Intermediate Similarity	NPC473199
0.8318	Intermediate Similarity	NPC210178
0.8318	Intermediate Similarity	NPC162033
0.8304	Intermediate Similarity	NPC244127
0.8304	Intermediate Similarity	NPC469820
0.8304	Intermediate Similarity	NPC469823
0.8304	Intermediate Similarity	NPC88945
0.8288	Intermediate Similarity	NPC251309
0.8286	Intermediate Similarity	NPC121072
0.8286	Intermediate Similarity	NPC21064
0.8276	Intermediate Similarity	NPC27363
0.8273	Intermediate Similarity	NPC274833
0.8273	Intermediate Similarity	NPC292196
0.8273	Intermediate Similarity	NPC122339
0.8273	Intermediate Similarity	NPC269466
0.8273	Intermediate Similarity	NPC270586
0.8273	Intermediate Similarity	NPC329953
0.8261	Intermediate Similarity	NPC470478
0.8257	Intermediate Similarity	NPC246205
0.8257	Intermediate Similarity	NPC137917
0.8257	Intermediate Similarity	NPC237503
0.8257	Intermediate Similarity	NPC306746
0.8257	Intermediate Similarity	NPC204407
0.8257	Intermediate Similarity	NPC167383
0.8257	Intermediate Similarity	NPC57362
0.8241	Intermediate Similarity	NPC283849
0.8241	Intermediate Similarity	NPC234160
0.8241	Intermediate Similarity	NPC186054
0.8235	Intermediate Similarity	NPC469754
0.8235	Intermediate Similarity	NPC471352
0.8235	Intermediate Similarity	NPC469751
0.8235	Intermediate Similarity	NPC10823
0.8235	Intermediate Similarity	NPC284406
0.8235	Intermediate Similarity	NPC469752
0.8235	Intermediate Similarity	NPC188234
0.8235	Intermediate Similarity	NPC471360
0.8235	Intermediate Similarity	NPC89514
0.8235	Intermediate Similarity	NPC6108
0.8235	Intermediate Similarity	NPC125077
0.8235	Intermediate Similarity	NPC471361
0.8235	Intermediate Similarity	NPC251866
0.8235	Intermediate Similarity	NPC70542
0.8235	Intermediate Similarity	NPC471358
0.8235	Intermediate Similarity	NPC471359
0.8235	Intermediate Similarity	NPC469755
0.8235	Intermediate Similarity	NPC140092
0.8235	Intermediate Similarity	NPC219085
0.8235	Intermediate Similarity	NPC9499
0.8235	Intermediate Similarity	NPC86159
0.8235	Intermediate Similarity	NPC17896
0.8235	Intermediate Similarity	NPC232785
0.8235	Intermediate Similarity	NPC197707
0.8235	Intermediate Similarity	NPC180079
0.8235	Intermediate Similarity	NPC469753
0.8235	Intermediate Similarity	NPC276838
0.8235	Intermediate Similarity	NPC329986
0.823	Intermediate Similarity	NPC156651
0.8224	Intermediate Similarity	NPC223741
0.8214	Intermediate Similarity	NPC473882
0.8214	Intermediate Similarity	NPC74727
0.8214	Intermediate Similarity	NPC116024
0.8214	Intermediate Similarity	NPC477580
0.8214	Intermediate Similarity	NPC220293
0.8214	Intermediate Similarity	NPC475633
0.8198	Intermediate Similarity	NPC207845
0.8198	Intermediate Similarity	NPC473303
0.8198	Intermediate Similarity	NPC100383
0.8198	Intermediate Similarity	NPC233003
0.8198	Intermediate Similarity	NPC471244
0.8198	Intermediate Similarity	NPC472719
0.8182	Intermediate Similarity	NPC476882
0.8182	Intermediate Similarity	NPC470065
0.8182	Intermediate Similarity	NPC199457
0.8182	Intermediate Similarity	NPC154856
0.8182	Intermediate Similarity	NPC476881
0.8182	Intermediate Similarity	NPC102914
0.8182	Intermediate Similarity	NPC127056
0.8182	Intermediate Similarity	NPC90856
0.8182	Intermediate Similarity	NPC475317
0.8182	Intermediate Similarity	NPC52241
0.8182	Intermediate Similarity	NPC110139
0.8182	Intermediate Similarity	NPC476880
0.8182	Intermediate Similarity	NPC164194
0.8182	Intermediate Similarity	NPC320383
0.8182	Intermediate Similarity	NPC474786
0.8182	Intermediate Similarity	NPC476886
0.8182	Intermediate Similarity	NPC279554
0.8182	Intermediate Similarity	NPC476883
0.8182	Intermediate Similarity	NPC476885
0.8182	Intermediate Similarity	NPC137104
0.8182	Intermediate Similarity	NPC270667
0.8182	Intermediate Similarity	NPC474589
0.8182	Intermediate Similarity	NPC29069
0.8182	Intermediate Similarity	NPC475296
0.8182	Intermediate Similarity	NPC56713
0.8182	Intermediate Similarity	NPC78046
0.8182	Intermediate Similarity	NPC274507
0.8182	Intermediate Similarity	NPC220984
0.8182	Intermediate Similarity	NPC75747
0.8182	Intermediate Similarity	NPC136877
0.8182	Intermediate Similarity	NPC471093
0.8182	Intermediate Similarity	NPC269095
0.8182	Intermediate Similarity	NPC7870
0.8182	Intermediate Similarity	NPC473324
0.8182	Intermediate Similarity	NPC59804
0.8182	Intermediate Similarity	NPC108709
0.8182	Intermediate Similarity	NPC68419
0.8182	Intermediate Similarity	NPC174679
0.8182	Intermediate Similarity	NPC476884
0.8182	Intermediate Similarity	NPC476887
0.8174	Intermediate Similarity	NPC470312
0.8174	Intermediate Similarity	NPC294112
0.8167	Intermediate Similarity	NPC253456
0.8167	Intermediate Similarity	NPC16569
0.8167	Intermediate Similarity	NPC159338
0.8165	Intermediate Similarity	NPC473410
0.8165	Intermediate Similarity	NPC38217
0.8165	Intermediate Similarity	NPC476123
0.8165	Intermediate Similarity	NPC472988
0.8165	Intermediate Similarity	NPC28198
0.8165	Intermediate Similarity	NPC177246
0.8165	Intermediate Similarity	NPC471094
0.8165	Intermediate Similarity	NPC469984
0.8165	Intermediate Similarity	NPC284807
0.8158	Intermediate Similarity	NPC45475
0.8155	Intermediate Similarity	NPC215570
0.8148	Intermediate Similarity	NPC165405
0.8142	Intermediate Similarity	NPC229752
0.8131	Intermediate Similarity	NPC139347
0.8125	Intermediate Similarity	NPC260665
0.8125	Intermediate Similarity	NPC471252
0.8125	Intermediate Similarity	NPC132668
0.8108	Intermediate Similarity	NPC473481
0.8108	Intermediate Similarity	NPC63244
0.8108	Intermediate Similarity	NPC164419
0.8108	Intermediate Similarity	NPC179434
0.8108	Intermediate Similarity	NPC108748
0.8108	Intermediate Similarity	NPC31839
0.8108	Intermediate Similarity	NPC297208
0.8108	Intermediate Similarity	NPC29505
0.8108	Intermediate Similarity	NPC30397
0.8108	Intermediate Similarity	NPC211798
0.8108	Intermediate Similarity	NPC235841
0.8108	Intermediate Similarity	NPC191763
0.8103	Intermediate Similarity	NPC202051
0.8103	Intermediate Similarity	NPC242840
0.8103	Intermediate Similarity	NPC31193
0.8099	Intermediate Similarity	NPC93416

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 NPC230888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	2165
0.2-0.3	4066
0.3-0.4	1749
0.4-0.5	478
0.5-0.6	259
0.6-0.7	168
0.7-0.8	50
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8448	Intermediate Similarity	NPD7507	Approved
0.8288	Intermediate Similarity	NPD8133	Approved
0.8235	Intermediate Similarity	NPD7319	Approved
0.8073	Intermediate Similarity	NPD6412	Phase 2
0.789	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD7736	Approved
0.7679	Intermediate Similarity	NPD6686	Approved
0.7667	Intermediate Similarity	NPD8328	Phase 3
0.7611	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD6370	Approved
0.7542	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD7328	Approved
0.7524	Intermediate Similarity	NPD8034	Phase 2
0.7524	Intermediate Similarity	NPD8035	Phase 2
0.7522	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD7516	Approved
0.7459	Intermediate Similarity	NPD7492	Approved
0.7458	Intermediate Similarity	NPD6009	Approved
0.7451	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8377	Approved
0.7417	Intermediate Similarity	NPD8294	Approved
0.7417	Intermediate Similarity	NPD6054	Approved
0.7414	Intermediate Similarity	NPD6882	Approved
0.7398	Intermediate Similarity	NPD6616	Approved
0.7355	Intermediate Similarity	NPD8033	Approved
0.7355	Intermediate Similarity	NPD8379	Approved
0.7355	Intermediate Similarity	NPD8296	Approved
0.7355	Intermediate Similarity	NPD8378	Approved
0.7355	Intermediate Similarity	NPD8380	Approved
0.7355	Intermediate Similarity	NPD8335	Approved
0.735	Intermediate Similarity	NPD4632	Approved
0.7339	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD6059	Approved
0.7273	Intermediate Similarity	NPD6319	Approved
0.7265	Intermediate Similarity	NPD8297	Approved
0.7227	Intermediate Similarity	NPD6940	Discontinued
0.7217	Intermediate Similarity	NPD6899	Approved
0.7217	Intermediate Similarity	NPD6881	Approved
0.7213	Intermediate Similarity	NPD7503	Approved
0.7213	Intermediate Similarity	NPD6016	Approved
0.7213	Intermediate Similarity	NPD6015	Approved
0.7193	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD5739	Approved
0.7193	Intermediate Similarity	NPD7128	Approved
0.7154	Intermediate Similarity	NPD5988	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD8171	Discontinued
0.713	Intermediate Similarity	NPD6399	Phase 3
0.7117	Intermediate Similarity	NPD7638	Approved
0.71	Intermediate Similarity	NPD6114	Approved
0.71	Intermediate Similarity	NPD6118	Approved
0.71	Intermediate Similarity	NPD6697	Approved
0.71	Intermediate Similarity	NPD6115	Approved
0.7094	Intermediate Similarity	NPD6883	Approved
0.7094	Intermediate Similarity	NPD7102	Approved
0.7094	Intermediate Similarity	NPD7290	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7054	Intermediate Similarity	NPD7640	Approved
0.7054	Intermediate Similarity	NPD7639	Approved
0.7034	Intermediate Similarity	NPD6869	Approved
0.7034	Intermediate Similarity	NPD8130	Phase 1
0.7034	Intermediate Similarity	NPD6847	Approved
0.7034	Intermediate Similarity	NPD6650	Approved
0.7034	Intermediate Similarity	NPD6649	Approved
0.7034	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD6012	Approved
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.7009	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6116	Phase 1
0.6983	Remote Similarity	NPD5701	Approved
0.696	Remote Similarity	NPD7604	Phase 2
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD5983	Phase 2
0.6935	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD6011	Approved
0.69	Remote Similarity	NPD6117	Approved
0.6885	Remote Similarity	NPD7115	Discovery
0.6881	Remote Similarity	NPD6079	Approved
0.6869	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5328	Approved
0.685	Remote Similarity	NPD6336	Discontinued
0.6825	Remote Similarity	NPD6067	Discontinued
0.6807	Remote Similarity	NPD4634	Approved
0.68	Remote Similarity	NPD6921	Approved
0.6796	Remote Similarity	NPD6928	Phase 2
0.6786	Remote Similarity	NPD4697	Phase 3
0.6757	Remote Similarity	NPD7748	Approved
0.6754	Remote Similarity	NPD5286	Approved
0.6754	Remote Similarity	NPD4696	Approved
0.6754	Remote Similarity	NPD5285	Approved
0.6752	Remote Similarity	NPD6008	Approved
0.675	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6033	Approved
0.6727	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD7515	Phase 2
0.6726	Remote Similarity	NPD6084	Phase 2
0.6726	Remote Similarity	NPD6083	Phase 2
0.6726	Remote Similarity	NPD7902	Approved
0.6726	Remote Similarity	NPD4755	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.664	Remote Similarity	NPD7101	Approved
0.664	Remote Similarity	NPD7100	Approved
0.6638	Remote Similarity	NPD4633	Approved
0.6638	Remote Similarity	NPD5226	Approved
0.6638	Remote Similarity	NPD5224	Approved
0.6638	Remote Similarity	NPD5211	Phase 2
0.6638	Remote Similarity	NPD5225	Approved
0.6637	Remote Similarity	NPD5221	Approved
0.6637	Remote Similarity	NPD5222	Approved
0.6637	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3703	Phase 2
0.6609	Remote Similarity	NPD4700	Approved
0.6606	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5174	Approved
0.6581	Remote Similarity	NPD5175	Approved
0.6579	Remote Similarity	NPD5173	Approved
0.656	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD5223	Approved
0.6545	Remote Similarity	NPD6101	Approved
0.6545	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6274	Approved
0.6532	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD6435	Approved
0.6509	Remote Similarity	NPD3667	Approved
0.65	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7632	Discontinued
0.648	Remote Similarity	NPD6317	Approved
0.6476	Remote Similarity	NPD7525	Registered
0.6475	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3702	Approved
0.646	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7900	Approved
0.6455	Remote Similarity	NPD5737	Approved
0.6455	Remote Similarity	NPD6672	Approved
0.6449	Remote Similarity	NPD4788	Approved
0.6434	Remote Similarity	NPD7122	Discontinued
0.6429	Remote Similarity	NPD6313	Approved
0.6429	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD6314	Approved
0.6423	Remote Similarity	NPD6053	Discontinued
0.6422	Remote Similarity	NPD6684	Approved
0.6422	Remote Similarity	NPD6409	Approved
0.6422	Remote Similarity	NPD3618	Phase 1
0.6422	Remote Similarity	NPD7521	Approved
0.6422	Remote Similarity	NPD5330	Approved
0.6422	Remote Similarity	NPD7334	Approved
0.6422	Remote Similarity	NPD7146	Approved
0.6415	Remote Similarity	NPD1779	Approved
0.6415	Remote Similarity	NPD1780	Approved
0.6406	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD6908	Approved
0.6404	Remote Similarity	NPD5695	Phase 3
0.6379	Remote Similarity	NPD5696	Approved
0.6372	Remote Similarity	NPD5779	Approved
0.6372	Remote Similarity	NPD4202	Approved
0.6372	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD3573	Approved
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	Approved
0.6321	Remote Similarity	NPD5368	Approved
0.6306	Remote Similarity	NPD6903	Approved
0.6303	Remote Similarity	NPD4754	Approved
0.63	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7641	Discontinued
0.6296	Remote Similarity	NPD3669	Approved
0.6296	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD8074	Phase 3
0.6283	Remote Similarity	NPD7983	Approved
0.6279	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5956	Approved
0.626	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8299	Approved
0.626	Remote Similarity	NPD8342	Approved
0.626	Remote Similarity	NPD5250	Approved
0.626	Remote Similarity	NPD5251	Approved
0.626	Remote Similarity	NPD5247	Approved
0.626	Remote Similarity	NPD5248	Approved
0.626	Remote Similarity	NPD8341	Approved
0.626	Remote Similarity	NPD5249	Phase 3
0.626	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6239	Remote Similarity	NPD3133	Approved
0.6239	Remote Similarity	NPD3666	Approved
0.6239	Remote Similarity	NPD3665	Phase 1
0.6239	Remote Similarity	NPD4225	Approved
0.623	Remote Similarity	NPD5128	Approved
0.6216	Remote Similarity	NPD7524	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