NPASS Compound

Structure

CID92327 OpenBabel06191715432D 22 25 0 0 1 0 0 0 0 0999 V2000 -4.3153 3.0018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5154 2.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3537 2.9011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8378 -1.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1904 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1901 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 1.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8375 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6770 1.9347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3535 1.9342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6756 -0.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6765 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5148 0.4832 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8384 0.4837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5151 1.4505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5418 -1.4670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 20 1 6 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 7 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 6 0 0 0 19 21 1 6 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.21
Volume:	335.791
LogP:	5.221
LogD:	4.618
LogS:	-4.892
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	4.468
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.567
MDCK Permeability:	3.2111984182847664e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	94.93871307373047%
Volume Distribution (VD):	0.933
Pgp-substrate:	5.225165367126465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.643
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.769
CYP2C19-substrate:	0.664
CYP2C9-inhibitor:	0.419
CYP2C9-substrate:	0.139
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.739

ADMET: Excretion

Clearance (CL):	5.053
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.965
Carcinogencity:	0.627
Eye Corrosion:	0.938
Eye Irritation:	0.889
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC92327

Natural Product ID:	NPC92327
*Common Name:**	Pregna-1,4,20-Trien-3-One
IUPAC Name:	(8S,9S,10R,13R,14S,17R)-17-ethenyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	KFTYFBOHSUEIEJ-NWSAAYAGSA-N
Standard InCHI:	InChI=1S/C21H28O/c1-4-14-6-8-18-17-7-5-15-13-16(22)9-11-21(15,3)19(17)10-12-20(14,18)2/h4,9,11,13-14,17-19H,1,5-8,10,12H2,2-3H3/t14-,17-,18-,19-,20+,21-/m0/s1
SMILES:	C=C[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689218
PubChem CID:	13034987
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins and derivatives

*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
NPO30138	Carijoa	Genus	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21235217]

☑ 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
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	40.0	ug.mL-1	PMID[490722]
NPT1246	Organism	Salmonella	Salmonella	MIC	=	40.0	ug.mL-1	PMID[490722]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	40.0	ug.mL-1	PMID[490722]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	40.0	ug.mL-1	PMID[490722]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	40.0	ug.mL-1	PMID[490722]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	40.0	ug.mL-1	PMID[490722]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	=	40.0	ug.mL-1	PMID[490722]

☑ 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 NPC92327 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	176
0.1-0.2	2288
0.2-0.3	15756
0.3-0.4	10929
0.4-0.5	7282
0.5-0.6	4600
0.6-0.7	1385
0.7-0.8	239
0.8-0.85	9
0.85-0.9	25
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC176107
0.9365	High Similarity	NPC176171
0.9104	High Similarity	NPC251705
0.8955	High Similarity	NPC54123
0.8955	High Similarity	NPC115023
0.8955	High Similarity	NPC234707
0.8852	High Similarity	NPC60772
0.8841	High Similarity	NPC293803
0.8824	High Similarity	NPC303613
0.8824	High Similarity	NPC470044
0.8824	High Similarity	NPC470045
0.8824	High Similarity	NPC474228
0.8806	High Similarity	NPC35734
0.8806	High Similarity	NPC265782
0.8806	High Similarity	NPC282593
0.8806	High Similarity	NPC159577
0.8806	High Similarity	NPC307176
0.8806	High Similarity	NPC251929
0.8806	High Similarity	NPC2634
0.8714	High Similarity	NPC474463
0.8714	High Similarity	NPC69408
0.8696	High Similarity	NPC309852
0.8676	High Similarity	NPC305501
0.8657	High Similarity	NPC139397
0.8657	High Similarity	NPC182815
0.8529	High Similarity	NPC260040
0.8507	High Similarity	NPC20610
0.8485	Intermediate Similarity	NPC323005
0.8472	Intermediate Similarity	NPC105197
0.8429	Intermediate Similarity	NPC255021
0.8406	Intermediate Similarity	NPC470078
0.8356	Intermediate Similarity	NPC190211
0.831	Intermediate Similarity	NPC255650
0.8243	Intermediate Similarity	NPC474509
0.8235	Intermediate Similarity	NPC188292
0.8235	Intermediate Similarity	NPC260474
0.8197	Intermediate Similarity	NPC5626
0.8182	Intermediate Similarity	NPC469662
0.8169	Intermediate Similarity	NPC474797
0.8169	Intermediate Similarity	NPC329866
0.8169	Intermediate Similarity	NPC474796
0.8143	Intermediate Similarity	NPC5701
0.8056	Intermediate Similarity	NPC473171
0.8033	Intermediate Similarity	NPC14002
0.803	Intermediate Similarity	NPC165695
0.803	Intermediate Similarity	NPC197238
0.803	Intermediate Similarity	NPC202118
0.8	Intermediate Similarity	NPC40574
0.8	Intermediate Similarity	NPC477856
0.8	Intermediate Similarity	NPC214770
0.7971	Intermediate Similarity	NPC87141
0.7971	Intermediate Similarity	NPC310992
0.7945	Intermediate Similarity	NPC469793
0.7945	Intermediate Similarity	NPC469796
0.791	Intermediate Similarity	NPC212210
0.7895	Intermediate Similarity	NPC6434
0.7887	Intermediate Similarity	NPC225467
0.7879	Intermediate Similarity	NPC213152
0.7867	Intermediate Similarity	NPC170793
0.7867	Intermediate Similarity	NPC90965
0.7857	Intermediate Similarity	NPC256846
0.7821	Intermediate Similarity	NPC33913
0.7794	Intermediate Similarity	NPC251118
0.7792	Intermediate Similarity	NPC472239
0.7746	Intermediate Similarity	NPC475728
0.7742	Intermediate Similarity	NPC23117
0.7733	Intermediate Similarity	NPC82635
0.7733	Intermediate Similarity	NPC470052
0.7727	Intermediate Similarity	NPC25853
0.7727	Intermediate Similarity	NPC127582
0.7722	Intermediate Similarity	NPC29447
0.7692	Intermediate Similarity	NPC469769
0.7647	Intermediate Similarity	NPC475124
0.7647	Intermediate Similarity	NPC285371
0.7639	Intermediate Similarity	NPC190035
0.7639	Intermediate Similarity	NPC181204
0.7639	Intermediate Similarity	NPC223187
0.7606	Intermediate Similarity	NPC477857
0.76	Intermediate Similarity	NPC91665
0.7595	Intermediate Similarity	NPC472265
0.7576	Intermediate Similarity	NPC472304
0.7576	Intermediate Similarity	NPC276764
0.7571	Intermediate Similarity	NPC475523
0.7564	Intermediate Similarity	NPC3511
0.7564	Intermediate Similarity	NPC142253
0.7564	Intermediate Similarity	NPC472867
0.7564	Intermediate Similarity	NPC100297
0.7564	Intermediate Similarity	NPC193347
0.7564	Intermediate Similarity	NPC320514
0.7532	Intermediate Similarity	NPC472478
0.7531	Intermediate Similarity	NPC93778
0.75	Intermediate Similarity	NPC472306
0.75	Intermediate Similarity	NPC288253
0.75	Intermediate Similarity	NPC469996
0.75	Intermediate Similarity	NPC123194
0.7467	Intermediate Similarity	NPC1254
0.7465	Intermediate Similarity	NPC142754
0.7465	Intermediate Similarity	NPC296697
0.7465	Intermediate Similarity	NPC82477
0.7465	Intermediate Similarity	NPC39157
0.7465	Intermediate Similarity	NPC155198
0.746	Intermediate Similarity	NPC295777
0.746	Intermediate Similarity	NPC69898
0.7429	Intermediate Similarity	NPC43300
0.7429	Intermediate Similarity	NPC96812
0.7429	Intermediate Similarity	NPC39462
0.7429	Intermediate Similarity	NPC168824
0.7429	Intermediate Similarity	NPC189917
0.7429	Intermediate Similarity	NPC107704
0.7424	Intermediate Similarity	NPC311852
0.7424	Intermediate Similarity	NPC266295
0.7424	Intermediate Similarity	NPC94991
0.7424	Intermediate Similarity	NPC56905
0.7424	Intermediate Similarity	NPC27610
0.7424	Intermediate Similarity	NPC30215
0.7391	Intermediate Similarity	NPC169275
0.7391	Intermediate Similarity	NPC52449
0.7375	Intermediate Similarity	NPC181743
0.7375	Intermediate Similarity	NPC237712
0.7375	Intermediate Similarity	NPC85774
0.7375	Intermediate Similarity	NPC214043
0.7375	Intermediate Similarity	NPC178025
0.7375	Intermediate Similarity	NPC16287
0.7375	Intermediate Similarity	NPC87552
0.7375	Intermediate Similarity	NPC144258
0.7368	Intermediate Similarity	NPC470557
0.7361	Intermediate Similarity	NPC286814
0.7349	Intermediate Similarity	NPC177141
0.7349	Intermediate Similarity	NPC262043
0.7342	Intermediate Similarity	NPC469799
0.7342	Intermediate Similarity	NPC469806
0.7342	Intermediate Similarity	NPC469804
0.7342	Intermediate Similarity	NPC469805
0.7333	Intermediate Similarity	NPC476346
0.7324	Intermediate Similarity	NPC220210
0.7324	Intermediate Similarity	NPC20181
0.7317	Intermediate Similarity	NPC476293
0.7317	Intermediate Similarity	NPC58063
0.7313	Intermediate Similarity	NPC259261
0.7308	Intermediate Similarity	NPC476809
0.7308	Intermediate Similarity	NPC469798
0.7308	Intermediate Similarity	NPC469797
0.7284	Intermediate Similarity	NPC8571
0.7284	Intermediate Similarity	NPC60350
0.7284	Intermediate Similarity	NPC469948
0.7284	Intermediate Similarity	NPC22133
0.7273	Intermediate Similarity	NPC267626
0.7273	Intermediate Similarity	NPC228911
0.7273	Intermediate Similarity	NPC49575
0.7273	Intermediate Similarity	NPC55004
0.7273	Intermediate Similarity	NPC115515
0.7273	Intermediate Similarity	NPC115385
0.7262	Intermediate Similarity	NPC273199
0.725	Intermediate Similarity	NPC3856
0.725	Intermediate Similarity	NPC41539
0.725	Intermediate Similarity	NPC279639
0.725	Intermediate Similarity	NPC474790
0.725	Intermediate Similarity	NPC474976
0.7246	Intermediate Similarity	NPC32285
0.7237	Intermediate Similarity	NPC292589
0.7237	Intermediate Similarity	NPC112680
0.7237	Intermediate Similarity	NPC113733
0.7237	Intermediate Similarity	NPC134330
0.7237	Intermediate Similarity	NPC129165
0.7215	Intermediate Similarity	NPC147066
0.7215	Intermediate Similarity	NPC477372
0.7206	Intermediate Similarity	NPC270042
0.72	Intermediate Similarity	NPC22134
0.72	Intermediate Similarity	NPC219232
0.72	Intermediate Similarity	NPC211641
0.72	Intermediate Similarity	NPC159497
0.72	Intermediate Similarity	NPC128346
0.7195	Intermediate Similarity	NPC475022
0.7195	Intermediate Similarity	NPC118648
0.7195	Intermediate Similarity	NPC222613
0.7195	Intermediate Similarity	NPC474778
0.7195	Intermediate Similarity	NPC31564
0.7195	Intermediate Similarity	NPC145879
0.7195	Intermediate Similarity	NPC474732
0.7195	Intermediate Similarity	NPC474733
0.7183	Intermediate Similarity	NPC259156
0.7183	Intermediate Similarity	NPC242945
0.7179	Intermediate Similarity	NPC472490
0.7179	Intermediate Similarity	NPC153987
0.7179	Intermediate Similarity	NPC44083
0.7179	Intermediate Similarity	NPC215843
0.7179	Intermediate Similarity	NPC170394
0.7176	Intermediate Similarity	NPC218301
0.7176	Intermediate Similarity	NPC272746
0.7164	Intermediate Similarity	NPC308108
0.7164	Intermediate Similarity	NPC170799
0.7162	Intermediate Similarity	NPC304983
0.7162	Intermediate Similarity	NPC474562
0.716	Intermediate Similarity	NPC473246
0.716	Intermediate Similarity	NPC321187
0.716	Intermediate Similarity	NPC227064
0.716	Intermediate Similarity	NPC329043
0.716	Intermediate Similarity	NPC161423
0.716	Intermediate Similarity	NPC58841
0.7143	Intermediate Similarity	NPC473902

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 NPC92327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2165
0.2-0.3	4896
0.3-0.4	1364
0.4-0.5	247
0.5-0.6	125
0.6-0.7	128
0.7-0.8	49
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8806	High Similarity	NPD4691	Approved
0.8806	High Similarity	NPD4747	Approved
0.8696	High Similarity	NPD4058	Approved
0.8657	High Similarity	NPD4137	Phase 3
0.8429	Intermediate Similarity	NPD4687	Approved
0.8356	Intermediate Similarity	NPD4195	Approved
0.8235	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD5733	Approved
0.8143	Intermediate Similarity	NPD5276	Approved
0.7564	Intermediate Similarity	NPD4221	Approved
0.7564	Intermediate Similarity	NPD4223	Phase 3
0.7468	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4785	Approved
0.7432	Intermediate Similarity	NPD4784	Approved
0.7407	Intermediate Similarity	NPD5690	Phase 2
0.7397	Intermediate Similarity	NPD4243	Approved
0.7375	Intermediate Similarity	NPD4197	Approved
0.7284	Intermediate Similarity	NPD5329	Approved
0.7195	Intermediate Similarity	NPD4689	Approved
0.7195	Intermediate Similarity	NPD4690	Approved
0.7195	Intermediate Similarity	NPD4138	Approved
0.7195	Intermediate Similarity	NPD4688	Approved
0.7195	Intermediate Similarity	NPD5205	Approved
0.7195	Intermediate Similarity	NPD4693	Phase 3
0.7176	Intermediate Similarity	NPD6079	Approved
0.7164	Intermediate Similarity	NPD287	Approved
0.716	Intermediate Similarity	NPD3133	Approved
0.716	Intermediate Similarity	NPD3665	Phase 1
0.716	Intermediate Similarity	NPD3666	Approved
0.7105	Intermediate Similarity	NPD4190	Phase 3
0.7105	Intermediate Similarity	NPD7339	Approved
0.7105	Intermediate Similarity	NPD6942	Approved
0.7105	Intermediate Similarity	NPD5275	Approved
0.7051	Intermediate Similarity	NPD3617	Approved
0.7024	Intermediate Similarity	NPD5208	Approved
0.7024	Intermediate Similarity	NPD6672	Approved
0.7024	Intermediate Similarity	NPD5737	Approved
0.6988	Remote Similarity	NPD5280	Approved
0.6988	Remote Similarity	NPD3618	Phase 1
0.6988	Remote Similarity	NPD6684	Approved
0.6988	Remote Similarity	NPD7521	Approved
0.6988	Remote Similarity	NPD6409	Approved
0.6988	Remote Similarity	NPD7334	Approved
0.6988	Remote Similarity	NPD5330	Approved
0.6988	Remote Similarity	NPD7146	Approved
0.6988	Remote Similarity	NPD4694	Approved
0.6988	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4786	Approved
0.6941	Remote Similarity	NPD6673	Approved
0.6941	Remote Similarity	NPD5328	Approved
0.6941	Remote Similarity	NPD6080	Approved
0.6941	Remote Similarity	NPD4753	Phase 2
0.6941	Remote Similarity	NPD6904	Approved
0.6932	Remote Similarity	NPD5210	Approved
0.6932	Remote Similarity	NPD4629	Approved
0.6914	Remote Similarity	NPD3667	Approved
0.6875	Remote Similarity	NPD4695	Discontinued
0.686	Remote Similarity	NPD5207	Approved
0.6854	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5222	Approved
0.6854	Remote Similarity	NPD5221	Approved
0.6824	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6903	Approved
0.68	Remote Similarity	NPD7144	Approved
0.68	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6939	Phase 2
0.68	Remote Similarity	NPD7143	Approved
0.6795	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8028	Phase 2
0.6786	Remote Similarity	NPD6098	Approved
0.6786	Remote Similarity	NPD4623	Approved
0.6786	Remote Similarity	NPD5279	Phase 3
0.6786	Remote Similarity	NPD4519	Discontinued
0.6782	Remote Similarity	NPD5284	Approved
0.6782	Remote Similarity	NPD5281	Approved
0.6782	Remote Similarity	NPD5694	Approved
0.6782	Remote Similarity	NPD5693	Phase 1
0.6778	Remote Similarity	NPD5173	Approved
0.6747	Remote Similarity	NPD3668	Phase 3
0.6711	Remote Similarity	NPD7151	Approved
0.6711	Remote Similarity	NPD7152	Approved
0.6711	Remote Similarity	NPD7150	Approved
0.6706	Remote Similarity	NPD3573	Approved
0.6705	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD4696	Approved
0.663	Remote Similarity	NPD5285	Approved
0.663	Remote Similarity	NPD5286	Approved
0.6629	Remote Similarity	NPD6001	Approved
0.6591	Remote Similarity	NPD6050	Approved
0.6559	Remote Similarity	NPD5223	Approved
0.6556	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5290	Discontinued
0.6489	Remote Similarity	NPD5224	Approved
0.6489	Remote Similarity	NPD4633	Approved
0.6489	Remote Similarity	NPD5211	Phase 2
0.6489	Remote Similarity	NPD5091	Approved
0.6489	Remote Similarity	NPD5225	Approved
0.6489	Remote Similarity	NPD5226	Approved
0.6484	Remote Similarity	NPD4697	Phase 3
0.6477	Remote Similarity	NPD4096	Approved
0.6463	Remote Similarity	NPD7525	Registered
0.6437	Remote Similarity	NPD4518	Approved
0.6429	Remote Similarity	NPD4788	Approved
0.6421	Remote Similarity	NPD5174	Approved
0.6421	Remote Similarity	NPD5175	Approved
0.6413	Remote Similarity	NPD6084	Phase 2
0.6413	Remote Similarity	NPD4755	Approved
0.6413	Remote Similarity	NPD6083	Phase 2
0.6393	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4191	Approved
0.6389	Remote Similarity	NPD4194	Approved
0.6389	Remote Similarity	NPD4193	Approved
0.6389	Remote Similarity	NPD4192	Approved
0.6386	Remote Similarity	NPD4139	Approved
0.6386	Remote Similarity	NPD4692	Approved
0.6374	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD6051	Approved
0.6354	Remote Similarity	NPD5141	Approved
0.6344	Remote Similarity	NPD5696	Approved
0.6333	Remote Similarity	NPD6399	Phase 3
0.6333	Remote Similarity	NPD5133	Approved
0.6329	Remote Similarity	NPD6924	Approved
0.6329	Remote Similarity	NPD6926	Approved
0.6296	Remote Similarity	NPD6932	Approved
0.6277	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD6614	Approved
0.6224	Remote Similarity	NPD5697	Approved
0.622	Remote Similarity	NPD7145	Approved
0.6196	Remote Similarity	NPD5654	Approved
0.6173	Remote Similarity	NPD6933	Approved
0.6162	Remote Similarity	NPD5168	Approved
0.6162	Remote Similarity	NPD6899	Approved
0.6162	Remote Similarity	NPD6011	Approved
0.6162	Remote Similarity	NPD4729	Approved
0.6162	Remote Similarity	NPD4730	Approved
0.6162	Remote Similarity	NPD6881	Approved
0.6136	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6013	Approved
0.61	Remote Similarity	NPD6014	Approved
0.61	Remote Similarity	NPD6012	Approved
0.6098	Remote Similarity	NPD5776	Phase 2
0.6098	Remote Similarity	NPD6925	Approved
0.6087	Remote Similarity	NPD5707	Approved
0.6082	Remote Similarity	NPD4754	Approved
0.6082	Remote Similarity	NPD6052	Approved
0.6071	Remote Similarity	NPD7514	Phase 3
0.6067	Remote Similarity	NPD4723	Approved
0.6067	Remote Similarity	NPD4722	Approved
0.6064	Remote Similarity	NPD5959	Approved
0.6064	Remote Similarity	NPD3495	Discontinued
0.6061	Remote Similarity	NPD8262	Approved
0.6044	Remote Similarity	NPD7515	Phase 2
0.604	Remote Similarity	NPD5249	Phase 3
0.604	Remote Similarity	NPD5250	Approved
0.604	Remote Similarity	NPD5251	Approved
0.604	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6883	Approved
0.604	Remote Similarity	NPD4634	Approved
0.604	Remote Similarity	NPD7290	Approved
0.604	Remote Similarity	NPD5248	Approved
0.604	Remote Similarity	NPD5135	Approved
0.604	Remote Similarity	NPD5247	Approved
0.604	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD5169	Approved
0.6024	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD6902	Approved
0.598	Remote Similarity	NPD6650	Approved
0.598	Remote Similarity	NPD8130	Phase 1
0.598	Remote Similarity	NPD5127	Approved
0.598	Remote Similarity	NPD5217	Approved
0.598	Remote Similarity	NPD6617	Approved
0.598	Remote Similarity	NPD6869	Approved
0.598	Remote Similarity	NPD5215	Approved
0.598	Remote Similarity	NPD5216	Approved
0.598	Remote Similarity	NPD6847	Approved
0.598	Remote Similarity	NPD6649	Approved
0.596	Remote Similarity	NPD5739	Approved
0.596	Remote Similarity	NPD6008	Approved
0.596	Remote Similarity	NPD4768	Approved
0.596	Remote Similarity	NPD7128	Approved
0.596	Remote Similarity	NPD6402	Approved
0.596	Remote Similarity	NPD6675	Approved
0.596	Remote Similarity	NPD4767	Approved
0.5952	Remote Similarity	NPD6929	Approved
0.5952	Remote Similarity	NPD6683	Phase 2
0.5952	Remote Similarity	NPD7645	Phase 2
0.5938	Remote Similarity	NPD6404	Discontinued
0.5922	Remote Similarity	NPD8297	Approved
0.5922	Remote Similarity	NPD6882	Approved
0.5915	Remote Similarity	NPD4219	Approved
0.5914	Remote Similarity	NPD7748	Approved
0.5914	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7900	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