NPASS Compound

Structure

NPC154452 OpenBabel07101719252D 35 39 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 -0.8660 4.5000 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 4.3301 2.5000 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 3.4641 2.0000 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 -0.0000 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 -0.8660 3.5000 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 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 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 -0.8660 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 2.0000 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 2 0 0 0 0 0 0 0 0 0 -1.7321 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 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 0.0000 3.0000 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 6 2 0 0 0 0 3 17 1 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 19 2 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 2 1 1 0 0 0 16 24 1 0 0 0 0 16 33 1 0 0 0 0 17 30 2 0 0 0 0 17 34 1 0 0 0 0 18 28 1 1 0 0 0 19 29 1 0 0 0 0 20 35 1 1 0 0 0 21 9 1 6 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 28 1 1 0 0 0 23 29 1 1 0 0 0 24 26 1 0 0 0 0 24 31 1 1 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 6 0 0 0 26 34 1 1 0 0 0 27 33 1 0 0 0 0 27 35 1 6 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.31
Volume:	512.19
LogP:	4.774
LogD:	4.357
LogS:	-5.081
# Rotatable Bonds:	5
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.447
Synthetic Accessibility Score:	4.899
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.765
MDCK Permeability:	2.44078146351967e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.89
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	94.71317291259766%
Volume Distribution (VD):	2.01
Pgp-substrate:	3.2902677059173584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.154
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.333
CYP3A4-inhibitor:	0.698
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	1.824
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.54
Human Hepatotoxicity (H-HT):	0.483
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.938
Carcinogencity:	0.288
Eye Corrosion:	0.006
Eye Irritation:	0.058
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC154452

Natural Product ID:	NPC154452
*Common Name:**	Stereonsteroid H
IUPAC Name:	[(2R,3S,4R,5R,6S)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-ethenyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl] acetate
Synonyms:	Stereonsteroid H
Standard InCHIKey:	CLTGDTVOPJESPX-LOQVMCIBSA-N
Standard InCHI:	InChI=1S/C29H44O6/c1-6-18-8-10-22-21-9-7-19-15-20(11-13-29(19,5)23(21)12-14-28(18,22)4)35-27-25(32)26(34-17(3)30)24(31)16(2)33-27/h6-7,16,18,20-27,31-32H,1,8-15H2,2-5H3/t16-,18-,20-,21-,22-,23-,24+,25-,26+,27-,28+,29-/m0/s1
SMILES:	C=C[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O[C@@H]1O[C@@H](C)[C@H]([C@H]([C@@H]1O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492412
PubChem CID:	11526004
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	=	5.3	ug ml-1	PMID[545056]
NPT168	Cell Line	P388	Mus musculus	IC50	=	5.4	ug.mL-1	PMID[545056]

☑ 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 NPC154452 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	198
0.1-0.2	1303
0.2-0.3	4868
0.3-0.4	12454
0.4-0.5	9298
0.5-0.6	6113
0.6-0.7	5032
0.7-0.8	2824
0.8-0.85	470
0.85-0.9	111
0.9-0.95	20
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC121072
0.9894	High Similarity	NPC21064
0.9474	High Similarity	NPC158088
0.9468	High Similarity	NPC207617
0.9368	High Similarity	NPC243728
0.9368	High Similarity	NPC473890
0.93	High Similarity	NPC295389
0.93	High Similarity	NPC295980
0.9278	High Similarity	NPC267510
0.9184	High Similarity	NPC272015
0.9175	High Similarity	NPC282669
0.9167	High Similarity	NPC473555
0.9167	High Similarity	NPC471770
0.9167	High Similarity	NPC278939
0.9158	High Similarity	NPC230347
0.9158	High Similarity	NPC286612
0.9158	High Similarity	NPC275310
0.91	High Similarity	NPC473199
0.9082	High Similarity	NPC470434
0.9072	High Similarity	NPC477928
0.9072	High Similarity	NPC157739
0.9029	High Similarity	NPC470748
0.9029	High Similarity	NPC114188
0.901	High Similarity	NPC234160
0.9	High Similarity	NPC31430
0.9	High Similarity	NPC85593
0.898	High Similarity	NPC317019
0.898	High Similarity	NPC469942
0.8922	High Similarity	NPC38217
0.8922	High Similarity	NPC472988
0.8889	High Similarity	NPC285231
0.8889	High Similarity	NPC21568
0.8878	High Similarity	NPC234287
0.8878	High Similarity	NPC280825
0.8857	High Similarity	NPC144068
0.8854	High Similarity	NPC211238
0.8854	High Similarity	NPC305160
0.8846	High Similarity	NPC285410
0.8846	High Similarity	NPC250481
0.8846	High Similarity	NPC263827
0.8835	High Similarity	NPC43976
0.8835	High Similarity	NPC296761
0.8835	High Similarity	NPC51925
0.8835	High Similarity	NPC154085
0.8835	High Similarity	NPC125361
0.8824	High Similarity	NPC33053
0.8812	High Similarity	NPC187400
0.8812	High Similarity	NPC75608
0.8812	High Similarity	NPC221562
0.8812	High Similarity	NPC93352
0.8812	High Similarity	NPC470885
0.88	High Similarity	NPC136816
0.8788	High Similarity	NPC7341
0.8788	High Similarity	NPC473200
0.8776	High Similarity	NPC239547
0.8776	High Similarity	NPC96597
0.8776	High Similarity	NPC91197
0.8776	High Similarity	NPC309503
0.8776	High Similarity	NPC155319
0.8776	High Similarity	NPC125551
0.8774	High Similarity	NPC477808
0.8774	High Similarity	NPC473882
0.875	High Similarity	NPC475317
0.875	High Similarity	NPC52241
0.875	High Similarity	NPC154856
0.875	High Similarity	NPC129340
0.8737	High Similarity	NPC159876
0.8725	High Similarity	NPC473476
0.8725	High Similarity	NPC181845
0.8725	High Similarity	NPC162033
0.8725	High Similarity	NPC309448
0.8725	High Similarity	NPC473923
0.8725	High Similarity	NPC242748
0.8725	High Similarity	NPC474569
0.8725	High Similarity	NPC470763
0.8725	High Similarity	NPC470767
0.8713	High Similarity	NPC473198
0.87	High Similarity	NPC129372
0.87	High Similarity	NPC88000
0.87	High Similarity	NPC309425
0.87	High Similarity	NPC4831
0.87	High Similarity	NPC47566
0.87	High Similarity	NPC472023
0.87	High Similarity	NPC470054
0.87	High Similarity	NPC160734
0.8692	High Similarity	NPC207637
0.8692	High Similarity	NPC63609
0.8692	High Similarity	NPC477031
0.8692	High Similarity	NPC146652
0.8687	High Similarity	NPC216260
0.8687	High Similarity	NPC5358
0.8679	High Similarity	NPC251309
0.8667	High Similarity	NPC65167
0.866	High Similarity	NPC178949
0.866	High Similarity	NPC96736
0.866	High Similarity	NPC477927
0.866	High Similarity	NPC72817
0.8654	High Similarity	NPC118225
0.8654	High Similarity	NPC265655
0.8654	High Similarity	NPC246205
0.8646	High Similarity	NPC48463
0.8641	High Similarity	NPC226642
0.8641	High Similarity	NPC283829
0.8641	High Similarity	NPC14704
0.8641	High Similarity	NPC230507
0.8641	High Similarity	NPC161676
0.8641	High Similarity	NPC305423
0.8641	High Similarity	NPC113044
0.8641	High Similarity	NPC470432
0.8641	High Similarity	NPC94272
0.8641	High Similarity	NPC190395
0.8632	High Similarity	NPC473058
0.8627	High Similarity	NPC470043
0.8627	High Similarity	NPC470058
0.8627	High Similarity	NPC223741
0.8627	High Similarity	NPC470057
0.8627	High Similarity	NPC173583
0.8627	High Similarity	NPC470064
0.8627	High Similarity	NPC470059
0.8627	High Similarity	NPC470062
0.8627	High Similarity	NPC470060
0.8627	High Similarity	NPC470768
0.8627	High Similarity	NPC470061
0.8614	High Similarity	NPC159036
0.8614	High Similarity	NPC288694
0.8614	High Similarity	NPC470053
0.8614	High Similarity	NPC312553
0.8611	High Similarity	NPC477807
0.8611	High Similarity	NPC203862
0.8586	High Similarity	NPC475032
0.8586	High Similarity	NPC475033
0.8585	High Similarity	NPC210420
0.8585	High Similarity	NPC474265
0.8585	High Similarity	NPC130427
0.8585	High Similarity	NPC233003
0.8571	High Similarity	NPC101450
0.8558	High Similarity	NPC476539
0.8558	High Similarity	NPC195708
0.8558	High Similarity	NPC476540
0.8558	High Similarity	NPC476541
0.8558	High Similarity	NPC476538
0.8558	High Similarity	NPC98696
0.8544	High Similarity	NPC472899
0.8544	High Similarity	NPC472900
0.8544	High Similarity	NPC472898
0.8544	High Similarity	NPC470055
0.8544	High Similarity	NPC470056
0.8544	High Similarity	NPC165405
0.8544	High Similarity	NPC210178
0.8544	High Similarity	NPC26798
0.8532	High Similarity	NPC475357
0.8532	High Similarity	NPC160888
0.8532	High Similarity	NPC475403
0.8529	High Similarity	NPC155010
0.8529	High Similarity	NPC189852
0.8529	High Similarity	NPC157659
0.8529	High Similarity	NPC16573
0.8529	High Similarity	NPC213190
0.8529	High Similarity	NPC475701
0.8529	High Similarity	NPC16520
0.8529	High Similarity	NPC473020
0.8529	High Similarity	NPC131479
0.8529	High Similarity	NPC114874
0.8529	High Similarity	NPC31907
0.8529	High Similarity	NPC211879
0.8529	High Similarity	NPC472252
0.8529	High Similarity	NPC286969
0.8529	High Similarity	NPC245280
0.8529	High Similarity	NPC8039
0.8529	High Similarity	NPC120123
0.8519	High Similarity	NPC244127
0.8515	High Similarity	NPC155974
0.8515	High Similarity	NPC475617
0.85	High Similarity	NPC470068
0.8491	Intermediate Similarity	NPC269466
0.8491	Intermediate Similarity	NPC292196
0.8476	Intermediate Similarity	NPC232054
0.8476	Intermediate Similarity	NPC477027
0.8476	Intermediate Similarity	NPC171073
0.8476	Intermediate Similarity	NPC6806
0.8476	Intermediate Similarity	NPC477070
0.8476	Intermediate Similarity	NPC42482
0.8476	Intermediate Similarity	NPC475550
0.8476	Intermediate Similarity	NPC194207
0.8476	Intermediate Similarity	NPC477026
0.8476	Intermediate Similarity	NPC40440
0.8476	Intermediate Similarity	NPC475333
0.8476	Intermediate Similarity	NPC218571
0.8476	Intermediate Similarity	NPC475670
0.8476	Intermediate Similarity	NPC70204
0.8476	Intermediate Similarity	NPC477069
0.8476	Intermediate Similarity	NPC248746
0.8476	Intermediate Similarity	NPC477809
0.8476	Intermediate Similarity	NPC84956
0.8476	Intermediate Similarity	NPC470433
0.8476	Intermediate Similarity	NPC102016
0.8476	Intermediate Similarity	NPC300557
0.8476	Intermediate Similarity	NPC302057
0.8476	Intermediate Similarity	NPC244086
0.8476	Intermediate Similarity	NPC306131

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 NPC154452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1495
0.2-0.3	4099
0.3-0.4	2269
0.4-0.5	618
0.5-0.6	238
0.6-0.7	214
0.7-0.8	47
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
0.8462	Intermediate Similarity	NPD6412	Phase 2
0.8198	Intermediate Similarity	NPD7328	Approved
0.8198	Intermediate Similarity	NPD7327	Approved
0.8142	Intermediate Similarity	NPD7503	Approved
0.8142	Intermediate Similarity	NPD8033	Approved
0.8125	Intermediate Similarity	NPD7516	Approved
0.8053	Intermediate Similarity	NPD8294	Approved
0.8053	Intermediate Similarity	NPD8377	Approved
0.7982	Intermediate Similarity	NPD8379	Approved
0.7982	Intermediate Similarity	NPD8335	Approved
0.7982	Intermediate Similarity	NPD8378	Approved
0.7982	Intermediate Similarity	NPD8296	Approved
0.7982	Intermediate Similarity	NPD8380	Approved
0.787	Intermediate Similarity	NPD6686	Approved
0.7798	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7507	Approved
0.7679	Intermediate Similarity	NPD8133	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7583	Intermediate Similarity	NPD7736	Approved
0.7521	Intermediate Similarity	NPD7319	Approved
0.7478	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6370	Approved
0.7395	Intermediate Similarity	NPD8328	Phase 3
0.7355	Intermediate Similarity	NPD8293	Discontinued
0.734	Intermediate Similarity	NPD7339	Approved
0.734	Intermediate Similarity	NPD6942	Approved
0.7333	Intermediate Similarity	NPD7492	Approved
0.7328	Intermediate Similarity	NPD6009	Approved
0.7327	Intermediate Similarity	NPD7524	Approved
0.729	Intermediate Similarity	NPD7638	Approved
0.7288	Intermediate Similarity	NPD6054	Approved
0.7281	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD6616	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD4632	Approved
0.7213	Intermediate Similarity	NPD7078	Approved
0.7212	Intermediate Similarity	NPD7637	Suspended
0.72	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4786	Approved
0.7179	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD8171	Discontinued
0.713	Intermediate Similarity	NPD8297	Approved
0.71	Intermediate Similarity	NPD6695	Phase 3
0.7083	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6016	Approved
0.7083	Intermediate Similarity	NPD6015	Approved
0.708	Intermediate Similarity	NPD6899	Approved
0.708	Intermediate Similarity	NPD6881	Approved
0.7063	Intermediate Similarity	NPD8449	Approved
0.7054	Intermediate Similarity	NPD5739	Approved
0.7054	Intermediate Similarity	NPD6675	Approved
0.7054	Intermediate Similarity	NPD6402	Approved
0.7054	Intermediate Similarity	NPD7128	Approved
0.7037	Intermediate Similarity	NPD6083	Phase 2
0.7037	Intermediate Similarity	NPD6084	Phase 2
0.7025	Intermediate Similarity	NPD5988	Approved
0.7008	Intermediate Similarity	NPD8450	Suspended
0.7	Intermediate Similarity	NPD3667	Approved
0.6991	Remote Similarity	NPD5697	Approved
0.6967	Remote Similarity	NPD6067	Discontinued
0.6957	Remote Similarity	NPD7290	Approved
0.6957	Remote Similarity	NPD6883	Approved
0.6957	Remote Similarity	NPD7102	Approved
0.6942	Remote Similarity	NPD8515	Approved
0.6942	Remote Similarity	NPD8517	Approved
0.6942	Remote Similarity	NPD8513	Phase 3
0.6942	Remote Similarity	NPD8516	Approved
0.693	Remote Similarity	NPD7320	Approved
0.6907	Remote Similarity	NPD6933	Approved
0.6897	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD6649	Approved
0.6897	Remote Similarity	NPD6617	Approved
0.6897	Remote Similarity	NPD6650	Approved
0.6897	Remote Similarity	NPD8130	Phase 1
0.6897	Remote Similarity	NPD6847	Approved
0.6887	Remote Similarity	NPD8035	Phase 2
0.6887	Remote Similarity	NPD8034	Phase 2
0.687	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD6014	Approved
0.687	Remote Similarity	NPD6372	Approved
0.687	Remote Similarity	NPD6012	Approved
0.687	Remote Similarity	NPD6013	Approved
0.6869	Remote Similarity	NPD6929	Approved
0.6869	Remote Similarity	NPD7645	Phase 2
0.6857	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD5701	Approved
0.6837	Remote Similarity	NPD6932	Approved
0.6829	Remote Similarity	NPD7604	Phase 2
0.6827	Remote Similarity	NPD7750	Discontinued
0.6827	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4225	Approved
0.6814	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5983	Phase 2
0.68	Remote Similarity	NPD6931	Approved
0.68	Remote Similarity	NPD6928	Phase 2
0.68	Remote Similarity	NPD6930	Phase 2
0.6796	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6011	Approved
0.6768	Remote Similarity	NPD7145	Approved
0.6762	Remote Similarity	NPD6672	Approved
0.6762	Remote Similarity	NPD5737	Approved
0.6762	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7748	Approved
0.6754	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6409	Approved
0.6731	Remote Similarity	NPD5330	Approved
0.6731	Remote Similarity	NPD6684	Approved
0.6731	Remote Similarity	NPD7521	Approved
0.6731	Remote Similarity	NPD7334	Approved
0.6731	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD6079	Approved
0.6729	Remote Similarity	NPD6411	Approved
0.6729	Remote Similarity	NPD7515	Phase 2
0.6727	Remote Similarity	NPD7902	Approved
0.6724	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6336	Discontinued
0.6701	Remote Similarity	NPD4784	Approved
0.6701	Remote Similarity	NPD6926	Approved
0.6701	Remote Similarity	NPD6924	Approved
0.6701	Remote Similarity	NPD4785	Approved
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5328	Approved
0.6697	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6638	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7632	Discontinued
0.6634	Remote Similarity	NPD7514	Phase 3
0.6614	Remote Similarity	NPD6033	Approved
0.661	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5286	Approved
0.6607	Remote Similarity	NPD5285	Approved
0.6607	Remote Similarity	NPD4696	Approved
0.6604	Remote Similarity	NPD6903	Approved
0.6577	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD7087	Discontinued
0.6571	Remote Similarity	NPD3618	Phase 1
0.6569	Remote Similarity	NPD6902	Approved
0.6562	Remote Similarity	NPD7144	Approved
0.6562	Remote Similarity	NPD7143	Approved
0.6555	Remote Similarity	NPD6053	Discontinued
0.6542	Remote Similarity	NPD6101	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4753	Phase 2
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD3668	Phase 3
0.6538	Remote Similarity	NPD3665	Phase 1
0.6535	Remote Similarity	NPD4195	Approved
0.6535	Remote Similarity	NPD6683	Phase 2
0.6529	Remote Similarity	NPD6940	Discontinued
0.6522	Remote Similarity	NPD7625	Phase 1
0.6518	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4202	Approved
0.6512	Remote Similarity	NPD5956	Approved
0.6504	Remote Similarity	NPD7100	Approved
0.6504	Remote Similarity	NPD7101	Approved
0.6495	Remote Similarity	NPD4243	Approved
0.6491	Remote Similarity	NPD5226	Approved
0.6491	Remote Similarity	NPD5225	Approved
0.6491	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD4633	Approved
0.6491	Remote Similarity	NPD5211	Phase 2
0.6486	Remote Similarity	NPD5222	Approved
0.6486	Remote Similarity	NPD5221	Approved
0.6486	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6698	Approved
0.6481	Remote Similarity	NPD46	Approved
0.6481	Remote Similarity	NPD7838	Discovery
0.6476	Remote Similarity	NPD6893	Approved
0.6471	Remote Similarity	NPD7332	Phase 2
0.646	Remote Similarity	NPD4700	Approved
0.6458	Remote Similarity	NPD6922	Approved
0.6458	Remote Similarity	NPD6923	Approved
0.6455	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7900	Approved
0.6435	Remote Similarity	NPD5174	Approved
0.6435	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD5173	Approved
0.6423	Remote Similarity	NPD6335	Approved
0.6422	Remote Similarity	NPD5284	Approved
0.6422	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD6098	Approved
0.6404	Remote Similarity	NPD5223	Approved
0.6396	Remote Similarity	NPD5210	Approved
0.6396	Remote Similarity	NPD4629	Approved
0.6393	Remote Similarity	NPD6868	Approved
0.6393	Remote Similarity	NPD6274	Approved
0.6389	Remote Similarity	NPD6080	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