NPASS Compound

Structure

NPC231529 OpenBabel07101718242D 37 42 0 0 1 0 0 0 0 0999 V2000 1.3930 2.1807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5642 0.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5527 -2.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4607 0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1409 -0.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9248 -0.5225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0588 0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1928 1.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3868 -3.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0588 -0.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3923 -3.1052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3268 -2.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5947 -0.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0276 1.2498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5660 0.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -1.7039 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4607 -1.5225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5947 -2.0225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4607 -0.5225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3268 0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1928 -1.5225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3106 -0.8911 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0598 0.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3268 -0.0225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7287 -1.5225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9855 -2.1916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1928 -0.5225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7287 -0.5225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9309 -0.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4607 1.4775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0588 -2.0225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6030 -0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7126 1.6333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0866 -2.6297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5335 0.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0588 -1.0225 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 36 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 26 1 6 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 25 1 6 0 0 0 19 24 1 6 0 0 0 20 24 1 0 0 0 0 20 30 2 0 0 0 0 21 27 1 6 0 0 0 21 31 1 0 0 0 0 22 29 1 1 0 0 0 22 32 1 0 0 0 0 23 33 2 0 0 0 0 23 37 1 0 0 0 0 24 27 1 6 0 0 0 25 26 1 1 0 0 0 26 34 1 6 0 0 0 27 36 1 1 0 0 0 28 25 1 6 0 0 0 28 35 1 0 0 0 0 29 28 1 6 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.27
Volume:	518.577
LogP:	2.109
LogD:	1.121
LogS:	-4.294
# Rotatable Bonds:	1
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	6.373
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
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:	-5.389
MDCK Permeability:	9.512765245744959e-06
Pgp-inhibitor:	0.197
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.39
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.748
Plasma Protein Binding (PPB):	26.949371337890625%
Volume Distribution (VD):	0.402
Pgp-substrate:	36.691566467285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	4.365
Half-life (T1/2):	0.617

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.264
Carcinogencity:	0.882
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC231529

Natural Product ID:	NPC231529
*Common Name:**	Jaborosalactone 12
IUPAC Name:	(2aR,3R,4R,5S,5aR,6aS,6bR,10aR,11R,12aS,12bS,12cS)-2a,4,5a,11-tetrahydroxy-10a-methoxy-3,3',4',6b,12c-pentamethylspiro[2,3,4,6,6a,10,11,12,12a,12b-decahydro-1H-benzo[j]aceanthrylene-5,5'-furan]-2',7-dione
Synonyms:	Jaborosalactone 12
Standard InCHIKey:	LPBGVQXHMJPFQN-GCXMASHBSA-N
Standard InCHI:	InChI=1S/C29H40O8/c1-14-15(2)29(37-23(14)33)22(32)16(3)26(34)11-9-18-17-12-21(31)27(36-6)10-7-8-20(30)24(27,4)19(17)13-28(29,35)25(18,26)5/h7-8,16-19,21-22,31-32,34-35H,9-13H2,1-6H3/t16-,17+,18+,19+,21-,22-,24+,25+,26-,27+,28-,29+/m1/s1
SMILES:	CO[C@@]12CC=CC(=O)[C@]2(C)[C@@H]2[C@@H](C[C@H]1O)[C@@H]1CC[C@@]3([C@]1([C@@](C2)(O)[C@@]1(OC(=O)C(=C1C)C)[C@@H]([C@H]3C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515984
PubChem CID:	11038588
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO29151	Jaborosa odonelliana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO29151	Jaborosa odonelliana	Species	Solanaceae	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
IC50	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	9.32	uM	PMID[476742]
NPT2	Others	Unspecified		Ratio	>	4.2	n.a.	PMID[476742]
NPT27	Others	Unspecified		IC50	>	39000.0	nM	PMID[476742]

☑ 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 NPC231529 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	275
0.1-0.2	1487
0.2-0.3	4163
0.3-0.4	6987
0.4-0.5	11395
0.5-0.6	8274
0.6-0.7	6358
0.7-0.8	3077
0.8-0.85	482
0.85-0.9	183
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC473979
0.9167	High Similarity	NPC269642
0.9098	High Similarity	NPC473635
0.9098	High Similarity	NPC293112
0.9091	High Similarity	NPC11895
0.9024	High Similarity	NPC287423
0.9024	High Similarity	NPC470882
0.9016	High Similarity	NPC172154
0.9016	High Similarity	NPC81736
0.9008	High Similarity	NPC170538
0.8952	High Similarity	NPC311534
0.8934	High Similarity	NPC469789
0.8926	High Similarity	NPC46570
0.8917	High Similarity	NPC475041
0.8906	High Similarity	NPC130447
0.8871	High Similarity	NPC471357
0.8871	High Similarity	NPC146456
0.8871	High Similarity	NPC469757
0.8871	High Similarity	NPC473265
0.8871	High Similarity	NPC117702
0.8862	High Similarity	NPC469790
0.8862	High Similarity	NPC473255
0.8862	High Similarity	NPC8369
0.8852	High Similarity	NPC222688
0.8852	High Similarity	NPC107493
0.8852	High Similarity	NPC23786
0.8852	High Similarity	NPC470265
0.8843	High Similarity	NPC251226
0.8843	High Similarity	NPC476961
0.8843	High Similarity	NPC472004
0.877	High Similarity	NPC159456
0.877	High Similarity	NPC67569
0.877	High Similarity	NPC4021
0.877	High Similarity	NPC310511
0.876	High Similarity	NPC230513
0.876	High Similarity	NPC473636
0.876	High Similarity	NPC77689
0.876	High Similarity	NPC5292
0.875	High Similarity	NPC134430
0.875	High Similarity	NPC55296
0.874	High Similarity	NPC471855
0.873	High Similarity	NPC471361
0.873	High Similarity	NPC180079
0.873	High Similarity	NPC469755
0.873	High Similarity	NPC471352
0.873	High Similarity	NPC469753
0.873	High Similarity	NPC6108
0.873	High Similarity	NPC197707
0.873	High Similarity	NPC10823
0.873	High Similarity	NPC89514
0.873	High Similarity	NPC70542
0.873	High Similarity	NPC221414
0.873	High Similarity	NPC17896
0.873	High Similarity	NPC9499
0.873	High Similarity	NPC284406
0.873	High Similarity	NPC470880
0.873	High Similarity	NPC469754
0.873	High Similarity	NPC471360
0.873	High Similarity	NPC251866
0.873	High Similarity	NPC471359
0.873	High Similarity	NPC86159
0.873	High Similarity	NPC219085
0.873	High Similarity	NPC469751
0.873	High Similarity	NPC471358
0.873	High Similarity	NPC469752
0.872	High Similarity	NPC473253
0.871	High Similarity	NPC8374
0.8689	High Similarity	NPC474585
0.8689	High Similarity	NPC79579
0.8689	High Similarity	NPC474370
0.8689	High Similarity	NPC154491
0.8689	High Similarity	NPC268530
0.8678	High Similarity	NPC153440
0.8678	High Similarity	NPC257457
0.8678	High Similarity	NPC311554
0.8667	High Similarity	NPC266728
0.8667	High Similarity	NPC49492
0.8667	High Similarity	NPC196931
0.8667	High Similarity	NPC190286
0.8667	High Similarity	NPC469794
0.8667	High Similarity	NPC72772
0.8655	High Similarity	NPC250109
0.8655	High Similarity	NPC962
0.8651	High Similarity	NPC473620
0.8629	High Similarity	NPC120724
0.8629	High Similarity	NPC27363
0.8615	High Similarity	NPC59288
0.8607	High Similarity	NPC61520
0.8607	High Similarity	NPC472667
0.8607	High Similarity	NPC475520
0.8607	High Similarity	NPC264954
0.8607	High Similarity	NPC42673
0.8607	High Similarity	NPC211093
0.8607	High Similarity	NPC473203
0.8607	High Similarity	NPC473839
0.8605	High Similarity	NPC476823
0.8595	High Similarity	NPC475809
0.8595	High Similarity	NPC239273
0.8595	High Similarity	NPC284068
0.8595	High Similarity	NPC470959
0.8595	High Similarity	NPC476965
0.8594	High Similarity	NPC34963
0.8594	High Similarity	NPC93416
0.8583	High Similarity	NPC175186
0.8583	High Similarity	NPC67259
0.8583	High Similarity	NPC35109
0.8583	High Similarity	NPC476966
0.8583	High Similarity	NPC104382
0.8583	High Similarity	NPC471407
0.8583	High Similarity	NPC147912
0.8571	High Similarity	NPC471356
0.8571	High Similarity	NPC179412
0.856	High Similarity	NPC24651
0.8548	High Similarity	NPC153700
0.8548	High Similarity	NPC88326
0.8537	High Similarity	NPC143755
0.8527	High Similarity	NPC157817
0.8527	High Similarity	NPC469673
0.8527	High Similarity	NPC469749
0.8527	High Similarity	NPC247190
0.8527	High Similarity	NPC146857
0.8527	High Similarity	NPC88668
0.8527	High Similarity	NPC225385
0.8527	High Similarity	NPC116075
0.8527	High Similarity	NPC58029
0.8527	High Similarity	NPC32793
0.8527	High Similarity	NPC104585
0.8527	High Similarity	NPC298783
0.8525	High Similarity	NPC50774
0.8525	High Similarity	NPC470420
0.8525	High Similarity	NPC473720
0.8525	High Similarity	NPC251310
0.8525	High Similarity	NPC709
0.8525	High Similarity	NPC329736
0.8516	High Similarity	NPC471170
0.8516	High Similarity	NPC159338
0.8516	High Similarity	NPC253456
0.8516	High Similarity	NPC220757
0.8516	High Similarity	NPC173347
0.8516	High Similarity	NPC279478
0.8516	High Similarity	NPC241935
0.8516	High Similarity	NPC196921
0.8516	High Similarity	NPC16569
0.8492	Intermediate Similarity	NPC203702
0.8492	Intermediate Similarity	NPC469750
0.8492	Intermediate Similarity	NPC250556
0.8492	Intermediate Similarity	NPC120994
0.8487	Intermediate Similarity	NPC94650
0.848	Intermediate Similarity	NPC67251
0.848	Intermediate Similarity	NPC18945
0.848	Intermediate Similarity	NPC91693
0.848	Intermediate Similarity	NPC105926
0.848	Intermediate Similarity	NPC204812
0.848	Intermediate Similarity	NPC55602
0.848	Intermediate Similarity	NPC265557
0.8468	Intermediate Similarity	NPC471999
0.8468	Intermediate Similarity	NPC470779
0.8468	Intermediate Similarity	NPC472000
0.8462	Intermediate Similarity	NPC329636
0.8455	Intermediate Similarity	NPC305260
0.8455	Intermediate Similarity	NPC476960
0.8455	Intermediate Similarity	NPC270850
0.845	Intermediate Similarity	NPC42670
0.845	Intermediate Similarity	NPC19124
0.8443	Intermediate Similarity	NPC97908
0.8443	Intermediate Similarity	NPC470492
0.8443	Intermediate Similarity	NPC470854
0.8443	Intermediate Similarity	NPC122033
0.8443	Intermediate Similarity	NPC471854
0.8443	Intermediate Similarity	NPC474654
0.8443	Intermediate Similarity	NPC286528
0.8443	Intermediate Similarity	NPC20302
0.8443	Intermediate Similarity	NPC140055
0.8443	Intermediate Similarity	NPC287343
0.8443	Intermediate Similarity	NPC167606
0.8438	Intermediate Similarity	NPC473593
0.8438	Intermediate Similarity	NPC91
0.843	Intermediate Similarity	NPC178289
0.843	Intermediate Similarity	NPC326542
0.843	Intermediate Similarity	NPC243354
0.8425	Intermediate Similarity	NPC42399
0.8425	Intermediate Similarity	NPC240070
0.8425	Intermediate Similarity	NPC329784
0.8417	Intermediate Similarity	NPC277769
0.8417	Intermediate Similarity	NPC269530
0.8417	Intermediate Similarity	NPC207251
0.8417	Intermediate Similarity	NPC470063
0.8413	Intermediate Similarity	NPC32868
0.8413	Intermediate Similarity	NPC476729
0.8413	Intermediate Similarity	NPC241456
0.8413	Intermediate Similarity	NPC470922
0.84	Intermediate Similarity	NPC312833
0.8397	Intermediate Similarity	NPC171619
0.8397	Intermediate Similarity	NPC194716
0.839	Intermediate Similarity	NPC218123
0.839	Intermediate Similarity	NPC112895
0.839	Intermediate Similarity	NPC273155
0.839	Intermediate Similarity	NPC231278
0.8387	Intermediate Similarity	NPC41123
0.8387	Intermediate Similarity	NPC114939

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 NPC231529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1641
0.2-0.3	3674
0.3-0.4	2311
0.4-0.5	695
0.5-0.6	320
0.6-0.7	155
0.7-0.8	106
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.873	High Similarity	NPD7319	Approved
0.8492	Intermediate Similarity	NPD7507	Approved
0.8443	Intermediate Similarity	NPD7115	Discovery
0.8387	Intermediate Similarity	NPD6319	Approved
0.8306	Intermediate Similarity	NPD7516	Approved
0.8226	Intermediate Similarity	NPD7328	Approved
0.8226	Intermediate Similarity	NPD7327	Approved
0.8217	Intermediate Similarity	NPD7736	Approved
0.8125	Intermediate Similarity	NPD7492	Approved
0.8115	Intermediate Similarity	NPD8297	Approved
0.8095	Intermediate Similarity	NPD6054	Approved
0.8062	Intermediate Similarity	NPD6616	Approved
0.8049	Intermediate Similarity	NPD4632	Approved
0.8033	Intermediate Similarity	NPD6649	Approved
0.8033	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD7078	Approved
0.7969	Intermediate Similarity	NPD6370	Approved
0.7934	Intermediate Similarity	NPD6881	Approved
0.7934	Intermediate Similarity	NPD6899	Approved
0.7934	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6016	Approved
0.7891	Intermediate Similarity	NPD8296	Approved
0.7891	Intermediate Similarity	NPD8033	Approved
0.7891	Intermediate Similarity	NPD8380	Approved
0.7891	Intermediate Similarity	NPD8378	Approved
0.7891	Intermediate Similarity	NPD8379	Approved
0.7891	Intermediate Similarity	NPD8335	Approved
0.7891	Intermediate Similarity	NPD6015	Approved
0.7869	Intermediate Similarity	NPD6372	Approved
0.7869	Intermediate Similarity	NPD6373	Approved
0.7869	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD5697	Approved
0.7829	Intermediate Similarity	NPD5988	Approved
0.7823	Intermediate Similarity	NPD6882	Approved
0.7812	Intermediate Similarity	NPD8377	Approved
0.7812	Intermediate Similarity	NPD6059	Approved
0.7812	Intermediate Similarity	NPD8294	Approved
0.7805	Intermediate Similarity	NPD6883	Approved
0.7805	Intermediate Similarity	NPD7290	Approved
0.7805	Intermediate Similarity	NPD4634	Approved
0.7805	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7102	Approved
0.7787	Intermediate Similarity	NPD7320	Approved
0.7769	Intermediate Similarity	NPD5739	Approved
0.7769	Intermediate Similarity	NPD6008	Approved
0.7769	Intermediate Similarity	NPD6675	Approved
0.7769	Intermediate Similarity	NPD7128	Approved
0.7769	Intermediate Similarity	NPD6402	Approved
0.7742	Intermediate Similarity	NPD6847	Approved
0.7742	Intermediate Similarity	NPD8130	Phase 1
0.7742	Intermediate Similarity	NPD6617	Approved
0.7742	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD8293	Discontinued
0.7724	Intermediate Similarity	NPD6012	Approved
0.7724	Intermediate Similarity	NPD6013	Approved
0.7724	Intermediate Similarity	NPD6014	Approved
0.7717	Intermediate Similarity	NPD6009	Approved
0.7712	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7642	Intermediate Similarity	NPD6011	Approved
0.7634	Intermediate Similarity	NPD7604	Phase 2
0.7615	Intermediate Similarity	NPD7503	Approved
0.7615	Intermediate Similarity	NPD5983	Phase 2
0.7561	Intermediate Similarity	NPD5701	Approved
0.7561	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6053	Discontinued
0.7521	Intermediate Similarity	NPD5211	Phase 2
0.7519	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD6686	Approved
0.7419	Intermediate Similarity	NPD6412	Phase 2
0.7417	Intermediate Similarity	NPD4225	Approved
0.7398	Intermediate Similarity	NPD5141	Approved
0.7381	Intermediate Similarity	NPD6371	Approved
0.7377	Intermediate Similarity	NPD5225	Approved
0.7377	Intermediate Similarity	NPD5226	Approved
0.7377	Intermediate Similarity	NPD5224	Approved
0.7377	Intermediate Similarity	NPD4633	Approved
0.7348	Intermediate Similarity	NPD6921	Approved
0.7333	Intermediate Similarity	NPD4755	Approved
0.7328	Intermediate Similarity	NPD7100	Approved
0.7328	Intermediate Similarity	NPD7101	Approved
0.7323	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5174	Approved
0.7317	Intermediate Similarity	NPD5175	Approved
0.7295	Intermediate Similarity	NPD5223	Approved
0.728	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6033	Approved
0.7252	Intermediate Similarity	NPD6335	Approved
0.7231	Intermediate Similarity	NPD6274	Approved
0.7222	Intermediate Similarity	NPD4730	Approved
0.7222	Intermediate Similarity	NPD4729	Approved
0.7218	Intermediate Similarity	NPD8517	Approved
0.7218	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD8516	Approved
0.7218	Intermediate Similarity	NPD8513	Phase 3
0.7218	Intermediate Similarity	NPD8515	Approved
0.7213	Intermediate Similarity	NPD4700	Approved
0.7209	Intermediate Similarity	NPD8133	Approved
0.7203	Intermediate Similarity	NPD6079	Approved
0.719	Intermediate Similarity	NPD6083	Phase 2
0.719	Intermediate Similarity	NPD6084	Phase 2
0.7176	Intermediate Similarity	NPD6317	Approved
0.7176	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7121	Intermediate Similarity	NPD6313	Approved
0.7121	Intermediate Similarity	NPD6314	Approved
0.7109	Intermediate Similarity	NPD5247	Approved
0.7109	Intermediate Similarity	NPD5251	Approved
0.7109	Intermediate Similarity	NPD5248	Approved
0.7109	Intermediate Similarity	NPD5249	Phase 3
0.7109	Intermediate Similarity	NPD5250	Approved
0.7097	Intermediate Similarity	NPD7632	Discontinued
0.7063	Intermediate Similarity	NPD4767	Approved
0.7063	Intermediate Similarity	NPD4768	Approved
0.7049	Intermediate Similarity	NPD7902	Approved
0.7034	Intermediate Similarity	NPD5328	Approved
0.7031	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7260	Phase 2
0.7	Intermediate Similarity	NPD4202	Approved
0.6992	Remote Similarity	NPD5696	Approved
0.6975	Remote Similarity	NPD5785	Approved
0.6967	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5222	Approved
0.6967	Remote Similarity	NPD5221	Approved
0.6963	Remote Similarity	NPD6908	Approved
0.6963	Remote Similarity	NPD6909	Approved
0.6953	Remote Similarity	NPD5128	Approved
0.6949	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6334	Approved
0.6944	Remote Similarity	NPD6333	Approved
0.6942	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6917	Remote Similarity	NPD7515	Phase 2
0.6911	Remote Similarity	NPD5173	Approved
0.6905	Remote Similarity	NPD4754	Approved
0.6885	Remote Similarity	NPD5695	Phase 3
0.6885	Remote Similarity	NPD4629	Approved
0.6885	Remote Similarity	NPD5210	Approved
0.6885	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7799	Discontinued
0.6846	Remote Similarity	NPD5135	Approved
0.6846	Remote Similarity	NPD5169	Approved
0.6846	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6868	Approved
0.6835	Remote Similarity	NPD8074	Phase 3
0.6829	Remote Similarity	NPD4697	Phase 3
0.6821	Remote Similarity	NPD7236	Approved
0.6809	Remote Similarity	NPD5956	Approved
0.6807	Remote Similarity	NPD6903	Approved
0.6803	Remote Similarity	NPD7900	Approved
0.6803	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6648	Approved
0.6794	Remote Similarity	NPD5127	Approved
0.678	Remote Similarity	NPD7521	Approved
0.678	Remote Similarity	NPD7146	Approved
0.678	Remote Similarity	NPD6684	Approved
0.678	Remote Similarity	NPD3618	Phase 1
0.678	Remote Similarity	NPD7334	Approved
0.678	Remote Similarity	NPD5330	Approved
0.678	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6409	Approved
0.6777	Remote Similarity	NPD8035	Phase 2
0.6777	Remote Similarity	NPD7637	Suspended
0.6777	Remote Similarity	NPD8034	Phase 2
0.6777	Remote Similarity	NPD5284	Approved
0.6777	Remote Similarity	NPD5693	Phase 1
0.6777	Remote Similarity	NPD5281	Approved
0.675	Remote Similarity	NPD4753	Phase 2
0.6739	Remote Similarity	NPD6067	Discontinued
0.6723	Remote Similarity	NPD3573	Approved
0.6721	Remote Similarity	NPD5779	Approved
0.6721	Remote Similarity	NPD5778	Approved
0.6713	Remote Similarity	NPD6845	Suspended
0.671	Remote Similarity	NPD7239	Suspended
0.6694	Remote Similarity	NPD46	Approved
0.6694	Remote Similarity	NPD6698	Approved
0.6691	Remote Similarity	NPD4522	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6642	Remote Similarity	NPD5167	Approved
0.6639	Remote Similarity	NPD6411	Approved
0.6639	Remote Similarity	NPD7983	Approved
0.6614	Remote Similarity	NPD1700	Approved
0.6612	Remote Similarity	NPD6673	Approved
0.6612	Remote Similarity	NPD6080	Approved
0.6612	Remote Similarity	NPD6904	Approved
0.661	Remote Similarity	NPD3133	Approved
0.661	Remote Similarity	NPD3665	Phase 1
0.661	Remote Similarity	NPD3666	Approved
0.661	Remote Similarity	NPD4786	Approved
0.6597	Remote Similarity	NPD8338	Approved
0.6589	Remote Similarity	NPD8170	Clinical (unspecified phase)

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