NPASS Compound

Structure

NPC222688 OpenBabel07101718322D 38 42 0 0 1 0 0 0 0 0999 V2000 -7.1222 -1.7691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3903 -5.2123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6502 -4.7382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -3.2248 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2267 -2.7636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8903 -4.3463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4836 -3.4328 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 -3.9680 0.0000 C 0 0 2 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 -8.0927 -3.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8581 -3.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -5.1453 -4.9190 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 -9.0063 -2.8569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9071 -4.0691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8848 -4.2418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 6 8 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 25 1 0 0 0 0 9 28 1 0 0 0 0 10 22 1 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 20 1 0 0 0 0 13 29 1 0 0 0 0 14 1 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 2 1 1 0 0 0 15 16 1 0 0 0 0 15 38 1 0 0 0 0 16 10 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 31 1 1 0 0 0 21 25 1 1 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 22 32 1 6 0 0 0 23 29 1 0 0 0 0 23 33 2 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 28 1 1 0 0 0 26 29 1 1 0 0 0 27 5 1 6 0 0 0 27 35 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.3
Volume:	538.56
LogP:	1.502
LogD:	0.236
LogS:	-3.261
# Rotatable Bonds:	4
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	5.802
Fsp3:	0.862
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.775
MDCK Permeability:	5.096976019558497e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.43
20% Bioavailability (F20%):	0.816
30% Bioavailability (F30%):	0.803

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.235
Plasma Protein Binding (PPB):	56.84114074707031%
Volume Distribution (VD):	0.626
Pgp-substrate:	24.685985565185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	2.63
Half-life (T1/2):	0.44

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.148
Carcinogencity:	0.142
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC222688

Natural Product ID:	NPC222688
*Common Name:**	(3S,4S,5R)-4-[(2R,3R)-2,3-Dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-Tetrahydroxy-10,13-Dimethyl-6-Oxo-1,2,3,4,9,11,12,15,16,17-Decahydrocyclopenta[A]Phenanthren-17-Yl]Butyl]-3,5-Dimethyloxolan-2-One
IUPAC Name:	(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one
Synonyms:
Standard InCHIKey:	YQCOGGGDJXBMBU-JIVHLSMOSA-N
Standard InCHI:	InChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1
SMILES:	C[C@H]1[C@H](C[C@H]([C@@](C)([C@H]2CC[C@]3(C4=CC(=O)[C@@]5(C[C@H]([C@H](C[C@]5(C)[C@H]4CC[C@]23C)O)O)O)O)O)O)[C@@H](C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494049
PubChem CID:	12442769
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant	n.a.	n.a.	PMID[10425119]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748375]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[450547]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[450547]
NPT2	Others	Unspecified		Activity	=	80.2	%	PMID[450547]
NPT2	Others	Unspecified		Activity	=	51.9	%	PMID[450547]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[450547]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[450547]

☑ 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 NPC222688 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	251
0.1-0.2	1423
0.2-0.3	4285
0.3-0.4	7719
0.4-0.5	12780
0.5-0.6	6741
0.6-0.7	6385
0.7-0.8	2728
0.8-0.85	288
0.85-0.9	87
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC109973
0.9464	High Similarity	NPC49492
0.9464	High Similarity	NPC266728
0.9286	High Similarity	NPC962
0.9286	High Similarity	NPC73300
0.9286	High Similarity	NPC108721
0.9115	High Similarity	NPC250109
0.9043	High Similarity	NPC471854
0.9035	High Similarity	NPC326542
0.9027	High Similarity	NPC207251
0.9027	High Similarity	NPC280782
0.9	High Similarity	NPC470882
0.8929	High Similarity	NPC11710
0.8889	High Similarity	NPC475041
0.886	High Similarity	NPC472002
0.8852	High Similarity	NPC231529
0.8843	High Similarity	NPC473265
0.8839	High Similarity	NPC217201
0.8824	High Similarity	NPC269642
0.8803	High Similarity	NPC251310
0.8803	High Similarity	NPC257457
0.8803	High Similarity	NPC311554
0.8793	High Similarity	NPC96312
0.8793	High Similarity	NPC251236
0.8793	High Similarity	NPC40632
0.8793	High Similarity	NPC328374
0.8793	High Similarity	NPC179626
0.8793	High Similarity	NPC474734
0.8783	High Similarity	NPC49451
0.8783	High Similarity	NPC317210
0.875	High Similarity	NPC473979
0.875	High Similarity	NPC59530
0.875	High Similarity	NPC475060
0.875	High Similarity	NPC477916
0.875	High Similarity	NPC135038
0.875	High Similarity	NPC83744
0.875	High Similarity	NPC43252
0.875	High Similarity	NPC220229
0.8718	High Similarity	NPC474654
0.8718	High Similarity	NPC287343
0.8718	High Similarity	NPC176513
0.8718	High Similarity	NPC97908
0.8718	High Similarity	NPC470854
0.8718	High Similarity	NPC470775
0.8718	High Similarity	NPC122033
0.8707	High Similarity	NPC473798
0.8699	High Similarity	NPC470880
0.8696	High Similarity	NPC474516
0.8689	High Similarity	NPC473253
0.8684	High Similarity	NPC76084
0.8678	High Similarity	NPC473255
0.8673	High Similarity	NPC329417
0.8667	High Similarity	NPC65858
0.8661	High Similarity	NPC476027
0.8661	High Similarity	NPC150531
0.8661	High Similarity	NPC85829
0.8661	High Similarity	NPC49958
0.8661	High Similarity	NPC97202
0.8661	High Similarity	NPC50692
0.8661	High Similarity	NPC149047
0.8661	High Similarity	NPC319077
0.8661	High Similarity	NPC260268
0.8661	High Similarity	NPC302607
0.8661	High Similarity	NPC48733
0.8661	High Similarity	NPC214264
0.8661	High Similarity	NPC171137
0.8661	High Similarity	NPC152695
0.8661	High Similarity	NPC202167
0.8661	High Similarity	NPC296945
0.8655	High Similarity	NPC112038
0.8655	High Similarity	NPC472004
0.8632	High Similarity	NPC207217
0.8632	High Similarity	NPC148458
0.8621	High Similarity	NPC52634
0.8621	High Similarity	NPC194100
0.8596	High Similarity	NPC214644
0.8596	High Similarity	NPC141350
0.8595	High Similarity	NPC67251
0.8595	High Similarity	NPC267822
0.8584	High Similarity	NPC144854
0.8584	High Similarity	NPC3316
0.8571	High Similarity	NPC209502
0.8571	High Similarity	NPC204833
0.856	High Similarity	NPC471855
0.8559	High Similarity	NPC473590
0.8547	High Similarity	NPC178289
0.8547	High Similarity	NPC117712
0.8525	High Similarity	NPC476729
0.8525	High Similarity	NPC169818
0.8522	High Similarity	NPC272898
0.8522	High Similarity	NPC473036
0.8512	High Similarity	NPC28532
0.8509	High Similarity	NPC472217
0.8509	High Similarity	NPC65941
0.8509	High Similarity	NPC277017
0.8509	High Similarity	NPC154608
0.8509	High Similarity	NPC192813
0.8509	High Similarity	NPC472219
0.8509	High Similarity	NPC472218
0.8496	Intermediate Similarity	NPC257353
0.8496	Intermediate Similarity	NPC323834
0.8496	Intermediate Similarity	NPC196528
0.8487	Intermediate Similarity	NPC472397
0.8487	Intermediate Similarity	NPC171905
0.8487	Intermediate Similarity	NPC204552
0.8487	Intermediate Similarity	NPC471125
0.8487	Intermediate Similarity	NPC470776
0.8487	Intermediate Similarity	NPC472758
0.8487	Intermediate Similarity	NPC17772
0.8487	Intermediate Similarity	NPC188667
0.8482	Intermediate Similarity	NPC140723
0.8482	Intermediate Similarity	NPC191892
0.8475	Intermediate Similarity	NPC152199
0.8475	Intermediate Similarity	NPC235539
0.8475	Intermediate Similarity	NPC196931
0.8475	Intermediate Similarity	NPC474046
0.8475	Intermediate Similarity	NPC134869
0.8475	Intermediate Similarity	NPC270958
0.8475	Intermediate Similarity	NPC470628
0.8475	Intermediate Similarity	NPC259306
0.8468	Intermediate Similarity	NPC473888
0.8462	Intermediate Similarity	NPC208998
0.8462	Intermediate Similarity	NPC202889
0.8462	Intermediate Similarity	NPC51978
0.8462	Intermediate Similarity	NPC7921
0.8455	Intermediate Similarity	NPC293112
0.845	Intermediate Similarity	NPC290746
0.845	Intermediate Similarity	NPC79250
0.8448	Intermediate Similarity	NPC146945
0.8448	Intermediate Similarity	NPC171888
0.8443	Intermediate Similarity	NPC18945
0.8443	Intermediate Similarity	NPC91693
0.8443	Intermediate Similarity	NPC105926
0.8443	Intermediate Similarity	NPC265557
0.843	Intermediate Similarity	NPC102822
0.843	Intermediate Similarity	NPC470921
0.843	Intermediate Similarity	NPC472401
0.843	Intermediate Similarity	NPC310511
0.843	Intermediate Similarity	NPC477046
0.8425	Intermediate Similarity	NPC476823
0.8421	Intermediate Similarity	NPC230541
0.8421	Intermediate Similarity	NPC165873
0.8417	Intermediate Similarity	NPC5989
0.8417	Intermediate Similarity	NPC475775
0.8417	Intermediate Similarity	NPC472933
0.8417	Intermediate Similarity	NPC275696
0.8417	Intermediate Similarity	NPC5991
0.8417	Intermediate Similarity	NPC476529
0.8417	Intermediate Similarity	NPC255081
0.8417	Intermediate Similarity	NPC471108
0.8417	Intermediate Similarity	NPC230513
0.8417	Intermediate Similarity	NPC9674
0.8417	Intermediate Similarity	NPC22628
0.8417	Intermediate Similarity	NPC19028
0.8407	Intermediate Similarity	NPC47281
0.8407	Intermediate Similarity	NPC471293
0.8403	Intermediate Similarity	NPC156252
0.8403	Intermediate Similarity	NPC55296
0.8403	Intermediate Similarity	NPC239273
0.84	Intermediate Similarity	NPC471407
0.8393	Intermediate Similarity	NPC22388
0.8393	Intermediate Similarity	NPC477915
0.839	Intermediate Similarity	NPC18547
0.839	Intermediate Similarity	NPC474906
0.839	Intermediate Similarity	NPC470919
0.839	Intermediate Similarity	NPC469877
0.8376	Intermediate Similarity	NPC289312
0.8376	Intermediate Similarity	NPC71348
0.8376	Intermediate Similarity	NPC126691
0.8376	Intermediate Similarity	NPC302146
0.8376	Intermediate Similarity	NPC11252
0.8376	Intermediate Similarity	NPC100267
0.8376	Intermediate Similarity	NPC475524
0.8374	Intermediate Similarity	NPC81736
0.8374	Intermediate Similarity	NPC172154
0.8374	Intermediate Similarity	NPC8369
0.8374	Intermediate Similarity	NPC24651
0.8374	Intermediate Similarity	NPC470922
0.8361	Intermediate Similarity	NPC19464
0.8361	Intermediate Similarity	NPC312833
0.8348	Intermediate Similarity	NPC94529
0.8348	Intermediate Similarity	NPC293850
0.8347	Intermediate Similarity	NPC109607
0.8347	Intermediate Similarity	NPC471126
0.8347	Intermediate Similarity	NPC157252
0.8347	Intermediate Similarity	NPC143755
0.8347	Intermediate Similarity	NPC471128
0.8347	Intermediate Similarity	NPC471406
0.8347	Intermediate Similarity	NPC107338
0.8347	Intermediate Similarity	NPC145182
0.8347	Intermediate Similarity	NPC474585
0.8346	Intermediate Similarity	NPC88668
0.8346	Intermediate Similarity	NPC469673
0.8333	Intermediate Similarity	NPC279478
0.8333	Intermediate Similarity	NPC297179
0.8333	Intermediate Similarity	NPC118638
0.8333	Intermediate Similarity	NPC196921
0.8333	Intermediate Similarity	NPC50535
0.8333	Intermediate Similarity	NPC241935
0.8333	Intermediate Similarity	NPC220757

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 NPC222688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1649
0.2-0.3	3872
0.3-0.4	2229
0.4-0.5	660
0.5-0.6	240
0.6-0.7	138
0.7-0.8	105
0.8-0.85	41
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD6373	Approved
0.8596	High Similarity	NPD6372	Approved
0.8509	High Similarity	NPD7320	Approved
0.8496	Intermediate Similarity	NPD7128	Approved
0.8496	Intermediate Similarity	NPD6675	Approved
0.8496	Intermediate Similarity	NPD5739	Approved
0.8496	Intermediate Similarity	NPD6402	Approved
0.8448	Intermediate Similarity	NPD6649	Approved
0.8448	Intermediate Similarity	NPD6650	Approved
0.8376	Intermediate Similarity	NPD8297	Approved
0.8348	Intermediate Similarity	NPD6899	Approved
0.8348	Intermediate Similarity	NPD6881	Approved
0.8347	Intermediate Similarity	NPD6319	Approved
0.8333	Intermediate Similarity	NPD6008	Approved
0.8305	Intermediate Similarity	NPD4632	Approved
0.8261	Intermediate Similarity	NPD5701	Approved
0.8261	Intermediate Similarity	NPD5697	Approved
0.8226	Intermediate Similarity	NPD7492	Approved
0.822	Intermediate Similarity	NPD6882	Approved
0.8205	Intermediate Similarity	NPD6883	Approved
0.8205	Intermediate Similarity	NPD7290	Approved
0.8205	Intermediate Similarity	NPD7102	Approved
0.8197	Intermediate Similarity	NPD6054	Approved
0.8197	Intermediate Similarity	NPD6059	Approved
0.816	Intermediate Similarity	NPD6616	Approved
0.8136	Intermediate Similarity	NPD6869	Approved
0.8136	Intermediate Similarity	NPD8130	Phase 1
0.8136	Intermediate Similarity	NPD6847	Approved
0.8136	Intermediate Similarity	NPD6617	Approved
0.812	Intermediate Similarity	NPD6014	Approved
0.812	Intermediate Similarity	NPD6012	Approved
0.812	Intermediate Similarity	NPD6013	Approved
0.8095	Intermediate Similarity	NPD8293	Discontinued
0.8095	Intermediate Similarity	NPD7078	Approved
0.807	Intermediate Similarity	NPD5211	Phase 2
0.8065	Intermediate Similarity	NPD6370	Approved
0.8036	Intermediate Similarity	NPD4755	Approved
0.8034	Intermediate Similarity	NPD6011	Approved
0.8031	Intermediate Similarity	NPD7736	Approved
0.8016	Intermediate Similarity	NPD7507	Approved
0.7984	Intermediate Similarity	NPD6015	Approved
0.7984	Intermediate Similarity	NPD6016	Approved
0.7983	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD7319	Approved
0.7951	Intermediate Similarity	NPD6009	Approved
0.7931	Intermediate Similarity	NPD5141	Approved
0.792	Intermediate Similarity	NPD5988	Approved
0.7899	Intermediate Similarity	NPD4634	Approved
0.7895	Intermediate Similarity	NPD4700	Approved
0.7895	Intermediate Similarity	NPD4696	Approved
0.7895	Intermediate Similarity	NPD5286	Approved
0.7895	Intermediate Similarity	NPD5285	Approved
0.7876	Intermediate Similarity	NPD6084	Phase 2
0.7876	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD7604	Phase 2
0.784	Intermediate Similarity	NPD5983	Phase 2
0.7823	Intermediate Similarity	NPD7516	Approved
0.7805	Intermediate Similarity	NPD7115	Discovery
0.7759	Intermediate Similarity	NPD5224	Approved
0.7759	Intermediate Similarity	NPD5225	Approved
0.7759	Intermediate Similarity	NPD5226	Approved
0.7759	Intermediate Similarity	NPD4633	Approved
0.7742	Intermediate Similarity	NPD7328	Approved
0.7742	Intermediate Similarity	NPD7327	Approved
0.7739	Intermediate Similarity	NPD7639	Approved
0.7739	Intermediate Similarity	NPD7640	Approved
0.7734	Intermediate Similarity	NPD6336	Discontinued
0.7731	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6274	Approved
0.7712	Intermediate Similarity	NPD4767	Approved
0.7712	Intermediate Similarity	NPD4768	Approved
0.7698	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5174	Approved
0.7692	Intermediate Similarity	NPD5175	Approved
0.768	Intermediate Similarity	NPD7100	Approved
0.768	Intermediate Similarity	NPD7101	Approved
0.7672	Intermediate Similarity	NPD5223	Approved
0.7667	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5696	Approved
0.7652	Intermediate Similarity	NPD7638	Approved
0.7623	Intermediate Similarity	NPD6053	Discontinued
0.7615	Intermediate Similarity	NPD6033	Approved
0.7603	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6335	Approved
0.7583	Intermediate Similarity	NPD4730	Approved
0.7583	Intermediate Similarity	NPD4729	Approved
0.7559	Intermediate Similarity	NPD6908	Approved
0.7559	Intermediate Similarity	NPD6909	Approved
0.7544	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5695	Phase 3
0.7542	Intermediate Similarity	NPD4754	Approved
0.7522	Intermediate Similarity	NPD6399	Phase 3
0.752	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7478	Intermediate Similarity	NPD4697	Phase 3
0.746	Intermediate Similarity	NPD6313	Approved
0.746	Intermediate Similarity	NPD6314	Approved
0.7459	Intermediate Similarity	NPD5251	Approved
0.7459	Intermediate Similarity	NPD5250	Approved
0.7459	Intermediate Similarity	NPD5248	Approved
0.7459	Intermediate Similarity	NPD5249	Phase 3
0.7459	Intermediate Similarity	NPD5247	Approved
0.7442	Intermediate Similarity	NPD8328	Phase 3
0.7438	Intermediate Similarity	NPD5128	Approved
0.7422	Intermediate Similarity	NPD8296	Approved
0.7422	Intermediate Similarity	NPD8380	Approved
0.7422	Intermediate Similarity	NPD8335	Approved
0.7422	Intermediate Similarity	NPD8378	Approved
0.7422	Intermediate Similarity	NPD8379	Approved
0.7422	Intermediate Similarity	NPD8033	Approved
0.7411	Intermediate Similarity	NPD4753	Phase 2
0.7411	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD4202	Approved
0.7355	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8377	Approved
0.7344	Intermediate Similarity	NPD8294	Approved
0.7328	Intermediate Similarity	NPD5222	Approved
0.7328	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5221	Approved
0.7281	Intermediate Similarity	NPD6079	Approved
0.7265	Intermediate Similarity	NPD5173	Approved
0.7258	Intermediate Similarity	NPD5215	Approved
0.7258	Intermediate Similarity	NPD5216	Approved
0.7258	Intermediate Similarity	NPD5217	Approved
0.7257	Intermediate Similarity	NPD6904	Approved
0.7257	Intermediate Similarity	NPD6673	Approved
0.7257	Intermediate Similarity	NPD6080	Approved
0.7241	Intermediate Similarity	NPD5210	Approved
0.7241	Intermediate Similarity	NPD4629	Approved
0.7213	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4225	Approved
0.7177	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5135	Approved
0.7177	Intermediate Similarity	NPD5169	Approved
0.7168	Intermediate Similarity	NPD6672	Approved
0.7168	Intermediate Similarity	NPD5737	Approved
0.7168	Intermediate Similarity	NPD6903	Approved
0.7167	Intermediate Similarity	NPD7632	Discontinued
0.7165	Intermediate Similarity	NPD6868	Approved
0.7155	Intermediate Similarity	NPD6001	Approved
0.7154	Intermediate Similarity	NPD6921	Approved
0.7154	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.713	Intermediate Similarity	NPD5693	Phase 1
0.712	Intermediate Similarity	NPD5127	Approved
0.7119	Intermediate Similarity	NPD7902	Approved
0.7109	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5329	Approved
0.7045	Intermediate Similarity	NPD6067	Discontinued
0.704	Intermediate Similarity	NPD6371	Approved
0.7018	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7748	Approved
0.6991	Remote Similarity	NPD6098	Approved
0.6983	Remote Similarity	NPD5284	Approved
0.6983	Remote Similarity	NPD7515	Phase 2
0.6983	Remote Similarity	NPD6050	Approved
0.6983	Remote Similarity	NPD5281	Approved
0.6964	Remote Similarity	NPD3665	Phase 1
0.6964	Remote Similarity	NPD3666	Approved
0.6964	Remote Similarity	NPD4197	Approved
0.6964	Remote Similarity	NPD4786	Approved
0.6964	Remote Similarity	NPD3133	Approved
0.6953	Remote Similarity	NPD5167	Approved
0.6942	Remote Similarity	NPD5344	Discontinued
0.6942	Remote Similarity	NPD1700	Approved
0.6934	Remote Similarity	NPD7260	Phase 2
0.6897	Remote Similarity	NPD5207	Approved
0.6897	Remote Similarity	NPD5692	Phase 3
0.6894	Remote Similarity	NPD8513	Phase 3
0.6894	Remote Similarity	NPD8515	Approved
0.6894	Remote Similarity	NPD8517	Approved
0.6894	Remote Similarity	NPD8516	Approved
0.6884	Remote Similarity	NPD6845	Suspended
0.6879	Remote Similarity	NPD6333	Approved
0.6879	Remote Similarity	NPD6334	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.6864	Remote Similarity	NPD7900	Approved
0.6864	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5956	Approved
0.6838	Remote Similarity	NPD8035	Phase 2
0.6838	Remote Similarity	NPD5694	Approved
0.6838	Remote Similarity	NPD7637	Suspended
0.6838	Remote Similarity	NPD8034	Phase 2
0.6786	Remote Similarity	NPD3667	Approved
0.6786	Remote Similarity	NPD4221	Approved
0.6786	Remote Similarity	NPD4223	Phase 3
0.6783	Remote Similarity	NPD7524	Approved
0.678	Remote Similarity	NPD5778	Approved
0.678	Remote Similarity	NPD5779	Approved
0.6746	Remote Similarity	NPD5168	Approved
0.6742	Remote Similarity	NPD4522	Approved
0.6724	Remote Similarity	NPD5208	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