NPASS Compound

Structure

NPC213737 OpenBabel07101718312D 36 40 0 0 1 0 0 0 0 0999 V2000 2.4049 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7957 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0526 2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6728 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1554 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 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 17 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 8 33 1 0 0 0 0 9 34 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 31 2 0 0 0 0 17 35 1 0 0 0 0 18 23 1 0 0 0 0 18 32 1 1 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 29 1 6 0 0 0 22 35 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 1 0 0 0 25 33 1 6 0 0 0 25 36 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 30 34 1 0 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.36
Volume:	534.759
LogP:	5.401
LogD:	4.335
LogS:	-4.869
# Rotatable Bonds:	4
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	5.325
Fsp3:	0.967
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.734
MDCK Permeability:	1.4493709386442788e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.462
30% Bioavailability (F30%):	0.729

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	83.21515655517578%
Volume Distribution (VD):	1.646
Pgp-substrate:	24.786718368530273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.662
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.424
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	8.806
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.282
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.614
Carcinogencity:	0.228
Eye Corrosion:	0.942
Eye Irritation:	0.077
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC213737

Natural Product ID:	NPC213737
*Common Name:**	(1R,3S,3As,4S,5As,5Br,7As,11As,11Br,13S,13As,13Bs)-4-Hydroxy-1,3-Dimethoxy-3,5B,8,8,11A,13A-Hexamethylicosahydrochryseno[2,1-C]Furan-13-Yl Acetate
IUPAC Name:	[(1R,3S,3aS,4S,5aS,5bR,7aS,11aS,11bR,13S,13aS,13bS)-4-hydroxy-1,3-dimethoxy-3,5b,8,8,11a,13a-hexamethyl-3a,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydro-1H-phenanthro[2,1-e][2]benzofuran-13-yl] acetate
Synonyms:
Standard InCHIKey:	NIILZHCBDSZLDK-XBHCBSLKSA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-17(31)35-22-16-20-27(4)13-10-12-26(2,3)19(27)11-14-28(20,5)21-15-18(32)23-24(29(21,22)6)25(33-8)36-30(23,7)34-9/h18-25,32H,10-16H2,1-9H3/t18-,19-,20+,21-,22-,23+,24+,25+,27-,28+,29+,30-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)[C@@H]2C[C@@H]([C@@H]3[C@H]([C@H](OC)O[C@]3(C)OC)[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503492
PubChem CID:	10983993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33404	phyllospongia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12502324]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	30.0	%	PMID[549974]

☑ 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 NPC213737 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	408
0.1-0.2	3644
0.2-0.3	11500
0.3-0.4	12293
0.4-0.5	5801
0.5-0.6	3991
0.6-0.7	3454
0.7-0.8	1456
0.8-0.85	116
0.85-0.9	26
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474346
1.0	High Similarity	NPC474284
1.0	High Similarity	NPC475820
1.0	High Similarity	NPC474253
0.987	High Similarity	NPC2096
0.987	High Similarity	NPC208912
0.9359	High Similarity	NPC475456
0.8916	High Similarity	NPC471410
0.8916	High Similarity	NPC471411
0.8795	High Similarity	NPC235402
0.8675	High Similarity	NPC473299
0.8675	High Similarity	NPC18953
0.8621	High Similarity	NPC475878
0.8537	High Similarity	NPC73515
0.8488	Intermediate Similarity	NPC470872
0.8462	Intermediate Similarity	NPC471374
0.8462	Intermediate Similarity	NPC471375
0.8462	Intermediate Similarity	NPC209798
0.8444	Intermediate Similarity	NPC237071
0.8444	Intermediate Similarity	NPC238796
0.8444	Intermediate Similarity	NPC203434
0.8427	Intermediate Similarity	NPC191915
0.8427	Intermediate Similarity	NPC151214
0.8415	Intermediate Similarity	NPC471216
0.8415	Intermediate Similarity	NPC471217
0.8395	Intermediate Similarity	NPC477577
0.8372	Intermediate Similarity	NPC62202
0.8372	Intermediate Similarity	NPC110365
0.8372	Intermediate Similarity	NPC213658
0.8372	Intermediate Similarity	NPC45833
0.837	Intermediate Similarity	NPC471427
0.837	Intermediate Similarity	NPC471428
0.837	Intermediate Similarity	NPC471426
0.837	Intermediate Similarity	NPC51579
0.8353	Intermediate Similarity	NPC290612
0.8333	Intermediate Similarity	NPC57964
0.8333	Intermediate Similarity	NPC94582
0.8333	Intermediate Similarity	NPC21897
0.8313	Intermediate Similarity	NPC71541
0.8295	Intermediate Similarity	NPC50443
0.8295	Intermediate Similarity	NPC18536
0.8293	Intermediate Similarity	NPC220379
0.8242	Intermediate Similarity	NPC296936
0.8242	Intermediate Similarity	NPC475785
0.8242	Intermediate Similarity	NPC475765
0.8242	Intermediate Similarity	NPC252056
0.8214	Intermediate Similarity	NPC296734
0.8193	Intermediate Similarity	NPC472951
0.8193	Intermediate Similarity	NPC472943
0.8182	Intermediate Similarity	NPC82955
0.8172	Intermediate Similarity	NPC470030
0.8171	Intermediate Similarity	NPC177343
0.8161	Intermediate Similarity	NPC43912
0.8161	Intermediate Similarity	NPC140446
0.8152	Intermediate Similarity	NPC470591
0.8152	Intermediate Similarity	NPC97867
0.8152	Intermediate Similarity	NPC472273
0.8111	Intermediate Similarity	NPC171741
0.8111	Intermediate Similarity	NPC211845
0.8111	Intermediate Similarity	NPC323231
0.8111	Intermediate Similarity	NPC182740
0.8111	Intermediate Similarity	NPC256104
0.8111	Intermediate Similarity	NPC470623
0.8111	Intermediate Similarity	NPC18724
0.8111	Intermediate Similarity	NPC475307
0.8111	Intermediate Similarity	NPC224003
0.8111	Intermediate Similarity	NPC122083
0.8095	Intermediate Similarity	NPC271572
0.8095	Intermediate Similarity	NPC474870
0.809	Intermediate Similarity	NPC473542
0.8085	Intermediate Similarity	NPC108227
0.8085	Intermediate Similarity	NPC475574
0.8085	Intermediate Similarity	NPC472081
0.8085	Intermediate Similarity	NPC476512
0.8072	Intermediate Similarity	NPC476176
0.8068	Intermediate Similarity	NPC263079
0.8068	Intermediate Similarity	NPC281004
0.8065	Intermediate Similarity	NPC292775
0.8046	Intermediate Similarity	NPC155531
0.8046	Intermediate Similarity	NPC215968
0.8043	Intermediate Similarity	NPC156377
0.8022	Intermediate Similarity	NPC148593
0.8022	Intermediate Similarity	NPC267238
0.8022	Intermediate Similarity	NPC253611
0.8022	Intermediate Similarity	NPC471373
0.8022	Intermediate Similarity	NPC77717
0.8	Intermediate Similarity	NPC470155
0.8	Intermediate Similarity	NPC154043
0.8	Intermediate Similarity	NPC134967
0.8	Intermediate Similarity	NPC60018
0.8	Intermediate Similarity	NPC202688
0.8	Intermediate Similarity	NPC210759
0.8	Intermediate Similarity	NPC307167
0.8	Intermediate Similarity	NPC477447
0.8	Intermediate Similarity	NPC470029
0.8	Intermediate Similarity	NPC114700
0.8	Intermediate Similarity	NPC229801
0.8	Intermediate Similarity	NPC5632
0.8	Intermediate Similarity	NPC310138
0.8	Intermediate Similarity	NPC149966
0.8	Intermediate Similarity	NPC477446
0.8	Intermediate Similarity	NPC470611
0.8	Intermediate Similarity	NPC59006
0.7979	Intermediate Similarity	NPC317019
0.7979	Intermediate Similarity	NPC146188
0.7978	Intermediate Similarity	NPC471459
0.7978	Intermediate Similarity	NPC20822
0.7978	Intermediate Similarity	NPC67653
0.7978	Intermediate Similarity	NPC473472
0.7978	Intermediate Similarity	NPC102725
0.7978	Intermediate Similarity	NPC131466
0.7976	Intermediate Similarity	NPC7479
0.7976	Intermediate Similarity	NPC248944
0.7976	Intermediate Similarity	NPC257296
0.7957	Intermediate Similarity	NPC278939
0.7957	Intermediate Similarity	NPC210157
0.7957	Intermediate Similarity	NPC472145
0.7957	Intermediate Similarity	NPC471770
0.7957	Intermediate Similarity	NPC473555
0.7955	Intermediate Similarity	NPC252714
0.7952	Intermediate Similarity	NPC471045
0.7935	Intermediate Similarity	NPC189575
0.7935	Intermediate Similarity	NPC471424
0.7935	Intermediate Similarity	NPC471429
0.7935	Intermediate Similarity	NPC106701
0.7935	Intermediate Similarity	NPC471425
0.7935	Intermediate Similarity	NPC205129
0.7931	Intermediate Similarity	NPC266651
0.7931	Intermediate Similarity	NPC232044
0.7931	Intermediate Similarity	NPC273290
0.7927	Intermediate Similarity	NPC107963
0.7917	Intermediate Similarity	NPC139181
0.7917	Intermediate Similarity	NPC476837
0.7917	Intermediate Similarity	NPC97260
0.7912	Intermediate Similarity	NPC311246
0.7912	Intermediate Similarity	NPC88962
0.7912	Intermediate Similarity	NPC149400
0.7912	Intermediate Similarity	NPC144790
0.7912	Intermediate Similarity	NPC167644
0.7907	Intermediate Similarity	NPC111582
0.7907	Intermediate Similarity	NPC241959
0.7907	Intermediate Similarity	NPC477285
0.7901	Intermediate Similarity	NPC74639
0.7901	Intermediate Similarity	NPC308489
0.7895	Intermediate Similarity	NPC476839
0.7895	Intermediate Similarity	NPC476838
0.7889	Intermediate Similarity	NPC279329
0.7889	Intermediate Similarity	NPC471370
0.7889	Intermediate Similarity	NPC223143
0.7889	Intermediate Similarity	NPC471371
0.7889	Intermediate Similarity	NPC65550
0.7882	Intermediate Similarity	NPC470156
0.7882	Intermediate Similarity	NPC470154
0.7872	Intermediate Similarity	NPC157739
0.7872	Intermediate Similarity	NPC472144
0.7857	Intermediate Similarity	NPC126753
0.7841	Intermediate Similarity	NPC83242
0.7841	Intermediate Similarity	NPC474008
0.7841	Intermediate Similarity	NPC477283
0.7835	Intermediate Similarity	NPC469827
0.7831	Intermediate Similarity	NPC212453
0.7826	Intermediate Similarity	NPC253268
0.7826	Intermediate Similarity	NPC473774
0.7826	Intermediate Similarity	NPC175
0.7826	Intermediate Similarity	NPC30687
0.7826	Intermediate Similarity	NPC473851
0.7826	Intermediate Similarity	NPC174024
0.7826	Intermediate Similarity	NPC24960
0.7826	Intermediate Similarity	NPC477224
0.7826	Intermediate Similarity	NPC45959
0.7826	Intermediate Similarity	NPC179859
0.7826	Intermediate Similarity	NPC475436
0.7826	Intermediate Similarity	NPC312678
0.7826	Intermediate Similarity	NPC305418
0.7826	Intermediate Similarity	NPC3538
0.7826	Intermediate Similarity	NPC131693
0.7826	Intermediate Similarity	NPC291547
0.7826	Intermediate Similarity	NPC113500
0.7826	Intermediate Similarity	NPC252253
0.7821	Intermediate Similarity	NPC476928
0.7816	Intermediate Similarity	NPC227260
0.7816	Intermediate Similarity	NPC237938
0.7816	Intermediate Similarity	NPC299963
0.7816	Intermediate Similarity	NPC219535
0.7812	Intermediate Similarity	NPC80640
0.7802	Intermediate Similarity	NPC204881
0.7802	Intermediate Similarity	NPC36372
0.7802	Intermediate Similarity	NPC293609
0.7802	Intermediate Similarity	NPC473830
0.7802	Intermediate Similarity	NPC476668
0.7802	Intermediate Similarity	NPC120539
0.7802	Intermediate Similarity	NPC473637
0.7791	Intermediate Similarity	NPC286719
0.7791	Intermediate Similarity	NPC477286
0.7789	Intermediate Similarity	NPC477972
0.7789	Intermediate Similarity	NPC477968
0.7789	Intermediate Similarity	NPC228251
0.7789	Intermediate Similarity	NPC80417
0.7789	Intermediate Similarity	NPC20113
0.7789	Intermediate Similarity	NPC219285

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 NPC213737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	3800
0.2-0.3	3399
0.3-0.4	881
0.4-0.5	338
0.5-0.6	241
0.6-0.7	58
0.7-0.8	26
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7976	Intermediate Similarity	NPD6928	Phase 2
0.7717	Intermediate Similarity	NPD8171	Discontinued
0.7529	Intermediate Similarity	NPD6697	Approved
0.7529	Intermediate Similarity	NPD6115	Approved
0.7529	Intermediate Similarity	NPD6118	Approved
0.7529	Intermediate Similarity	NPD6114	Approved
0.7412	Intermediate Similarity	NPD6116	Phase 1
0.73	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6117	Approved
0.7111	Intermediate Similarity	NPD3669	Approved
0.7111	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1811	Approved
0.7059	Intermediate Similarity	NPD1810	Approved
0.7019	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8133	Approved
0.6905	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD7991	Discontinued
0.6818	Remote Similarity	NPD7328	Approved
0.6818	Remote Similarity	NPD7327	Approved
0.6789	Remote Similarity	NPD6940	Discontinued
0.6782	Remote Similarity	NPD3703	Phase 2
0.6774	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7516	Approved
0.6706	Remote Similarity	NPD2686	Approved
0.6706	Remote Similarity	NPD2687	Approved
0.6706	Remote Similarity	NPD2254	Approved
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6637	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD8033	Approved
0.6637	Remote Similarity	NPD8335	Approved
0.6637	Remote Similarity	NPD8296	Approved
0.6637	Remote Similarity	NPD8380	Approved
0.6637	Remote Similarity	NPD8379	Approved
0.6634	Remote Similarity	NPD7638	Approved
0.6628	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6522	Remote Similarity	NPD1780	Approved
0.6522	Remote Similarity	NPD8328	Phase 3
0.6522	Remote Similarity	NPD1779	Approved
0.6509	Remote Similarity	NPD6412	Phase 2
0.6484	Remote Similarity	NPD7645	Phase 2
0.6449	Remote Similarity	NPD6686	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6441	Remote Similarity	NPD7736	Approved
0.6437	Remote Similarity	NPD5777	Approved
0.641	Remote Similarity	NPD7507	Approved
0.64	Remote Similarity	NPD7748	Approved
0.6373	Remote Similarity	NPD7902	Approved
0.6364	Remote Similarity	NPD7515	Phase 2
0.6348	Remote Similarity	NPD7503	Approved
0.6322	Remote Similarity	NPD4245	Approved
0.6322	Remote Similarity	NPD4787	Phase 1
0.6322	Remote Similarity	NPD4244	Approved
0.625	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD6081	Approved
0.6237	Remote Similarity	NPD7525	Registered
0.6235	Remote Similarity	NPD4224	Phase 2
0.6222	Remote Similarity	NPD3702	Approved
0.6218	Remote Similarity	NPD8293	Discontinued
0.6207	Remote Similarity	NPD3698	Phase 2
0.619	Remote Similarity	NPD371	Approved
0.6154	Remote Similarity	NPD6370	Approved
0.6147	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4789	Approved
0.6095	Remote Similarity	NPD8418	Phase 2
0.6092	Remote Similarity	NPD5360	Phase 3
0.6092	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7900	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.605	Remote Similarity	NPD7492	Approved
0.6022	Remote Similarity	NPD3671	Phase 1
0.6	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD6059	Approved
0.5983	Remote Similarity	NPD6054	Approved
0.598	Remote Similarity	NPD6399	Phase 3
0.5966	Remote Similarity	NPD6067	Discontinued
0.5963	Remote Similarity	NPD7128	Approved
0.5963	Remote Similarity	NPD6402	Approved
0.5963	Remote Similarity	NPD6675	Approved
0.5963	Remote Similarity	NPD5739	Approved
0.595	Remote Similarity	NPD7078	Approved
0.593	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD1700	Approved
0.5862	Remote Similarity	NPD6009	Approved
0.5856	Remote Similarity	NPD6881	Approved
0.5856	Remote Similarity	NPD6899	Approved
0.5856	Remote Similarity	NPD7320	Approved
0.5856	Remote Similarity	NPD8174	Phase 2
0.5849	Remote Similarity	NPD4225	Approved
0.5804	Remote Similarity	NPD6373	Approved
0.5804	Remote Similarity	NPD6372	Approved
0.5798	Remote Similarity	NPD6015	Approved
0.5798	Remote Similarity	NPD6016	Approved
0.5784	Remote Similarity	NPD6700	Approved
0.5784	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5697	Approved
0.5766	Remote Similarity	NPD5701	Approved
0.5766	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7102	Approved
0.5752	Remote Similarity	NPD6883	Approved
0.5752	Remote Similarity	NPD7290	Approved
0.575	Remote Similarity	NPD5988	Approved
0.5732	Remote Similarity	NPD2267	Suspended
0.5728	Remote Similarity	NPD6703	Approved
0.5728	Remote Similarity	NPD6702	Approved
0.5714	Remote Similarity	NPD4758	Discontinued
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6649	Approved
0.5702	Remote Similarity	NPD6650	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.57	Remote Similarity	NPD8308	Discontinued
0.5684	Remote Similarity	NPD4802	Phase 2
0.5684	Remote Similarity	NPD4238	Approved
0.5684	Remote Similarity	NPD5364	Discontinued
0.5676	Remote Similarity	NPD6008	Approved
0.5667	Remote Similarity	NPD8516	Approved
0.5667	Remote Similarity	NPD8517	Approved
0.5667	Remote Similarity	NPD8513	Phase 3
0.5667	Remote Similarity	NPD8515	Approved
0.5664	Remote Similarity	NPD6012	Approved
0.5664	Remote Similarity	NPD6013	Approved
0.5664	Remote Similarity	NPD6014	Approved
0.5657	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8297	Approved
0.5625	Remote Similarity	NPD5354	Approved
0.5625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6083	Phase 2
0.5607	Remote Similarity	NPD6084	Phase 2
0.5603	Remote Similarity	NPD4632	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