NPASS Compound

Structure

NPC91439 OpenBabel07101718322D 35 38 0 0 1 0 0 0 0 0999 V2000 -6.1270 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8950 0.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3950 1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2256 0.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0766 1.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7997 0.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6270 3.5007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6629 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3950 -0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5289 0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2658 1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9309 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7969 -1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3950 2.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2610 3.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9931 1.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1270 -0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2610 0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1270 1.6347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9931 0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6629 -0.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2686 1.7818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9309 -0.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2610 1.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3950 1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2948 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7969 0.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1270 2.6347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6629 -1.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8591 -0.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2314 2.6478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1270 2.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1629 -2.2314 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 18 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 20 25 1 0 0 0 0 20 29 1 6 0 0 0 21 31 2 0 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 27 1 0 0 0 0 23 32 1 6 0 0 0 24 28 1 1 0 0 0 24 35 1 0 0 0 0 25 19 1 6 0 0 0 25 26 1 0 0 0 0 27 35 1 0 0 0 0 28 6 1 1 0 0 0 29 7 1 6 0 0 0 29 33 1 0 0 0 0 30 8 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	5.57
LogD:	3.968
LogS:	-3.19
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.245
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.706
MDCK Permeability:	1.4153586562315468e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	84.43009185791016%
Volume Distribution (VD):	0.791
Pgp-substrate:	10.398505210876465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	15.289
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.815
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.572
Carcinogencity:	0.919
Eye Corrosion:	0.007
Eye Irritation:	0.012
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: NPC91439

Natural Product ID:	NPC91439
*Common Name:**	Sipholenol K
IUPAC Name:	(4aR,8S,8aS)-4-[2-[(3S,5aS,6S,7S,9aS)-3,7-dihydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepin-6-yl]ethyl]-8-hydroxy-3,5,5,8-tetramethyl-4a,6,7,8a-tetrahydro-1H-naphthalen-2-one
Synonyms:	Sipholenol K
Standard InCHIKey:	AJXZQEWVCRNBOL-APVYCEMNSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-18-19(25-20(17-21(18)31)29(7,33)16-15-26(25,2)3)9-10-22-28(6)13-11-23(32)27(4,5)35-24(28)12-14-30(22,8)34/h20,22-25,32-34H,9-17H2,1-8H3/t20-,22-,23-,24-,25+,28-,29-,30-/m0/s1
SMILES:	CC1=C(CC[C@H]2[C@]3(C)CC[C@@H](C(C)(C)O[C@H]3CC[C@]2(C)O)O)[C@@H]2[C@H](CC1=O)[C@](C)(CCC2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557043
PubChem CID:	44234697
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	1.3	n.a.	PMID[503718]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	290.0	n.a.	PMID[503718]

☑ 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 NPC91439 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	248
0.1-0.2	1695
0.2-0.3	5369
0.3-0.4	10211
0.4-0.5	11488
0.5-0.6	6552
0.6-0.7	5923
0.7-0.8	1194
0.8-0.85	13
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC272451
0.85	High Similarity	NPC65523
0.8478	Intermediate Similarity	NPC233744
0.8478	Intermediate Similarity	NPC189777
0.8333	Intermediate Similarity	NPC212812
0.8286	Intermediate Similarity	NPC234042
0.8286	Intermediate Similarity	NPC152117
0.8252	Intermediate Similarity	NPC94942
0.8235	Intermediate Similarity	NPC181357
0.8235	Intermediate Similarity	NPC102352
0.82	Intermediate Similarity	NPC97435
0.8173	Intermediate Similarity	NPC87335
0.8155	Intermediate Similarity	NPC144854
0.8155	Intermediate Similarity	NPC3316
0.8144	Intermediate Similarity	NPC103527
0.8125	Intermediate Similarity	NPC73457
0.8125	Intermediate Similarity	NPC473166
0.8125	Intermediate Similarity	NPC248913
0.8113	Intermediate Similarity	NPC474516
0.8113	Intermediate Similarity	NPC472002
0.8105	Intermediate Similarity	NPC77263
0.8105	Intermediate Similarity	NPC250592
0.8077	Intermediate Similarity	NPC277017
0.8077	Intermediate Similarity	NPC469916
0.8077	Intermediate Similarity	NPC472439
0.8077	Intermediate Similarity	NPC154608
0.8077	Intermediate Similarity	NPC192813
0.8065	Intermediate Similarity	NPC290731
0.8065	Intermediate Similarity	NPC197823
0.8061	Intermediate Similarity	NPC200702
0.8041	Intermediate Similarity	NPC274046
0.8041	Intermediate Similarity	NPC198074
0.8039	Intermediate Similarity	NPC478057
0.8039	Intermediate Similarity	NPC99266
0.8039	Intermediate Similarity	NPC239716
0.8037	Intermediate Similarity	NPC317210
0.8021	Intermediate Similarity	NPC136801
0.8	Intermediate Similarity	NPC27814
0.8	Intermediate Similarity	NPC472802
0.8	Intermediate Similarity	NPC299590
0.8	Intermediate Similarity	NPC310546
0.7981	Intermediate Similarity	NPC469318
0.7981	Intermediate Similarity	NPC473173
0.7981	Intermediate Similarity	NPC473165
0.7979	Intermediate Similarity	NPC476217
0.7963	Intermediate Similarity	NPC247069
0.7963	Intermediate Similarity	NPC326542
0.7961	Intermediate Similarity	NPC470838
0.7959	Intermediate Similarity	NPC196227
0.7959	Intermediate Similarity	NPC111015
0.7959	Intermediate Similarity	NPC293086
0.7944	Intermediate Similarity	NPC207251
0.7941	Intermediate Similarity	NPC22388
0.7941	Intermediate Similarity	NPC165250
0.7941	Intermediate Similarity	NPC137430
0.7938	Intermediate Similarity	NPC155304
0.7938	Intermediate Similarity	NPC116726
0.7938	Intermediate Similarity	NPC210268
0.7925	Intermediate Similarity	NPC76084
0.7925	Intermediate Similarity	NPC474567
0.7921	Intermediate Similarity	NPC154072
0.7921	Intermediate Similarity	NPC167974
0.7905	Intermediate Similarity	NPC217201
0.7905	Intermediate Similarity	NPC151393
0.7905	Intermediate Similarity	NPC272576
0.7905	Intermediate Similarity	NPC293850
0.7895	Intermediate Similarity	NPC469317
0.7895	Intermediate Similarity	NPC241875
0.7895	Intermediate Similarity	NPC469314
0.7895	Intermediate Similarity	NPC138756
0.789	Intermediate Similarity	NPC16081
0.789	Intermediate Similarity	NPC96312
0.789	Intermediate Similarity	NPC40632
0.789	Intermediate Similarity	NPC328374
0.789	Intermediate Similarity	NPC173686
0.789	Intermediate Similarity	NPC251236
0.7885	Intermediate Similarity	NPC97202
0.7885	Intermediate Similarity	NPC470587
0.7885	Intermediate Similarity	NPC150531
0.7885	Intermediate Similarity	NPC477877
0.7885	Intermediate Similarity	NPC319077
0.7885	Intermediate Similarity	NPC49958
0.7885	Intermediate Similarity	NPC260268
0.7885	Intermediate Similarity	NPC302607
0.7885	Intermediate Similarity	NPC202167
0.7885	Intermediate Similarity	NPC48733
0.7885	Intermediate Similarity	NPC214264
0.7885	Intermediate Similarity	NPC171137
0.7885	Intermediate Similarity	NPC152695
0.7885	Intermediate Similarity	NPC476027
0.7885	Intermediate Similarity	NPC296945
0.7885	Intermediate Similarity	NPC85829
0.7885	Intermediate Similarity	NPC50692
0.7879	Intermediate Similarity	NPC30677
0.7879	Intermediate Similarity	NPC37787
0.7879	Intermediate Similarity	NPC473415
0.7879	Intermediate Similarity	NPC473170
0.7879	Intermediate Similarity	NPC469329
0.7879	Intermediate Similarity	NPC180557
0.7879	Intermediate Similarity	NPC271195
0.787	Intermediate Similarity	NPC208998
0.787	Intermediate Similarity	NPC49451
0.787	Intermediate Similarity	NPC962
0.787	Intermediate Similarity	NPC7921
0.787	Intermediate Similarity	NPC178981
0.787	Intermediate Similarity	NPC250109
0.7864	Intermediate Similarity	NPC282233
0.7864	Intermediate Similarity	NPC264048
0.7864	Intermediate Similarity	NPC159533
0.7864	Intermediate Similarity	NPC95585
0.7864	Intermediate Similarity	NPC8196
0.7857	Intermediate Similarity	NPC477435
0.7857	Intermediate Similarity	NPC477436
0.785	Intermediate Similarity	NPC171888
0.785	Intermediate Similarity	NPC146945
0.7843	Intermediate Similarity	NPC233012
0.7843	Intermediate Similarity	NPC54909
0.783	Intermediate Similarity	NPC11710
0.7818	Intermediate Similarity	NPC287343
0.7818	Intermediate Similarity	NPC474654
0.7818	Intermediate Similarity	NPC122033
0.7818	Intermediate Similarity	NPC470854
0.7818	Intermediate Similarity	NPC97908
0.7812	Intermediate Similarity	NPC230387
0.781	Intermediate Similarity	NPC475060
0.781	Intermediate Similarity	NPC67321
0.781	Intermediate Similarity	NPC187435
0.781	Intermediate Similarity	NPC230541
0.781	Intermediate Similarity	NPC83744
0.781	Intermediate Similarity	NPC143609
0.781	Intermediate Similarity	NPC202524
0.781	Intermediate Similarity	NPC220229
0.78	Intermediate Similarity	NPC469545
0.78	Intermediate Similarity	NPC61369
0.78	Intermediate Similarity	NPC8803
0.78	Intermediate Similarity	NPC7124
0.78	Intermediate Similarity	NPC473158
0.78	Intermediate Similarity	NPC5532
0.78	Intermediate Similarity	NPC260223
0.7798	Intermediate Similarity	NPC143268
0.7798	Intermediate Similarity	NPC473798
0.7798	Intermediate Similarity	NPC268238
0.7798	Intermediate Similarity	NPC323821
0.7798	Intermediate Similarity	NPC45218
0.7789	Intermediate Similarity	NPC472985
0.7789	Intermediate Similarity	NPC73038
0.7789	Intermediate Similarity	NPC472986
0.7789	Intermediate Similarity	NPC158393
0.7788	Intermediate Similarity	NPC204833
0.7788	Intermediate Similarity	NPC209502
0.7788	Intermediate Similarity	NPC471293
0.7778	Intermediate Similarity	NPC269530
0.7778	Intermediate Similarity	NPC67831
0.7778	Intermediate Similarity	NPC174051
0.7778	Intermediate Similarity	NPC472976
0.7778	Intermediate Similarity	NPC245972
0.7778	Intermediate Similarity	NPC471967
0.7778	Intermediate Similarity	NPC196485
0.7778	Intermediate Similarity	NPC42658
0.7778	Intermediate Similarity	NPC472977
0.7778	Intermediate Similarity	NPC477253
0.7778	Intermediate Similarity	NPC90769
0.7778	Intermediate Similarity	NPC318332
0.7767	Intermediate Similarity	NPC295791
0.7767	Intermediate Similarity	NPC478176
0.7757	Intermediate Similarity	NPC210005
0.7757	Intermediate Similarity	NPC250956
0.7757	Intermediate Similarity	NPC5284
0.7755	Intermediate Similarity	NPC111883
0.7755	Intermediate Similarity	NPC235704
0.7748	Intermediate Similarity	NPC251310
0.7745	Intermediate Similarity	NPC472972
0.7745	Intermediate Similarity	NPC307954
0.7742	Intermediate Similarity	NPC212083
0.7736	Intermediate Similarity	NPC329417
0.7736	Intermediate Similarity	NPC258323
0.7732	Intermediate Similarity	NPC32830
0.7732	Intermediate Similarity	NPC115607
0.7732	Intermediate Similarity	NPC97103
0.7727	Intermediate Similarity	NPC134869
0.7727	Intermediate Similarity	NPC207217
0.7727	Intermediate Similarity	NPC266728
0.7727	Intermediate Similarity	NPC235539
0.7727	Intermediate Similarity	NPC49492
0.7727	Intermediate Similarity	NPC152199
0.7723	Intermediate Similarity	NPC43686
0.7723	Intermediate Similarity	NPC175351
0.7723	Intermediate Similarity	NPC259788
0.7723	Intermediate Similarity	NPC89225
0.7723	Intermediate Similarity	NPC20078
0.7723	Intermediate Similarity	NPC121402
0.7723	Intermediate Similarity	NPC132753
0.7723	Intermediate Similarity	NPC27105
0.7723	Intermediate Similarity	NPC151681
0.7723	Intermediate Similarity	NPC224356
0.7723	Intermediate Similarity	NPC255589
0.7723	Intermediate Similarity	NPC473574
0.7714	Intermediate Similarity	NPC149047
0.7714	Intermediate Similarity	NPC96377
0.7714	Intermediate Similarity	NPC472655

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 NPC91439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2139
0.2-0.3	3894
0.3-0.4	1928
0.4-0.5	531
0.5-0.6	199
0.6-0.7	188
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD3618	Phase 1
0.7757	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7902	Approved
0.7642	Intermediate Similarity	NPD6412	Phase 2
0.76	Intermediate Similarity	NPD7748	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7551	Intermediate Similarity	NPD5328	Approved
0.7545	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7477	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6079	Approved
0.7383	Intermediate Similarity	NPD6675	Approved
0.7383	Intermediate Similarity	NPD7128	Approved
0.7383	Intermediate Similarity	NPD5739	Approved
0.7383	Intermediate Similarity	NPD6402	Approved
0.7379	Intermediate Similarity	NPD4755	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7308	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.7304	Intermediate Similarity	NPD6059	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7282	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD4634	Approved
0.7265	Intermediate Similarity	NPD8328	Phase 3
0.7248	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6899	Approved
0.7248	Intermediate Similarity	NPD6881	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7639	Approved
0.7238	Intermediate Similarity	NPD4696	Approved
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD5285	Approved
0.7238	Intermediate Similarity	NPD5286	Approved
0.7238	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD6008	Approved
0.7216	Intermediate Similarity	NPD4786	Approved
0.7216	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD3133	Approved
0.7216	Intermediate Similarity	NPD3666	Approved
0.7207	Intermediate Similarity	NPD6649	Approved
0.7207	Intermediate Similarity	NPD6650	Approved
0.7193	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7193	Intermediate Similarity	NPD6009	Approved
0.7188	Intermediate Similarity	NPD3667	Approved
0.7179	Intermediate Similarity	NPD6370	Approved
0.717	Intermediate Similarity	NPD5223	Approved
0.7156	Intermediate Similarity	NPD5701	Approved
0.7156	Intermediate Similarity	NPD5697	Approved
0.7119	Intermediate Similarity	NPD7604	Phase 2
0.7117	Intermediate Similarity	NPD7290	Approved
0.7117	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7102	Approved
0.7115	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5221	Approved
0.7115	Intermediate Similarity	NPD5222	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7103	Intermediate Similarity	NPD5224	Approved
0.7103	Intermediate Similarity	NPD5211	Phase 2
0.7103	Intermediate Similarity	NPD5226	Approved
0.7103	Intermediate Similarity	NPD5225	Approved
0.7103	Intermediate Similarity	NPD4633	Approved
0.7094	Intermediate Similarity	NPD5983	Phase 2
0.7094	Intermediate Similarity	NPD6015	Approved
0.7094	Intermediate Similarity	NPD6016	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD6011	Approved
0.7059	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6084	Phase 2
0.7048	Intermediate Similarity	NPD5173	Approved
0.7048	Intermediate Similarity	NPD6083	Phase 2
0.7037	Intermediate Similarity	NPD5174	Approved
0.7037	Intermediate Similarity	NPD5175	Approved
0.7037	Intermediate Similarity	NPD4754	Approved
0.7034	Intermediate Similarity	NPD5988	Approved
0.703	Intermediate Similarity	NPD4753	Phase 2
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD6336	Discontinued
0.6991	Remote Similarity	NPD6882	Approved
0.6975	Remote Similarity	NPD6067	Discontinued
0.6972	Remote Similarity	NPD5141	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6942	Remote Similarity	NPD8293	Discontinued
0.6942	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.69	Remote Similarity	NPD7146	Approved
0.69	Remote Similarity	NPD6409	Approved
0.69	Remote Similarity	NPD7334	Approved
0.69	Remote Similarity	NPD7521	Approved
0.69	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD6684	Approved
0.6893	Remote Similarity	NPD8034	Phase 2
0.6893	Remote Similarity	NPD8035	Phase 2
0.6885	Remote Similarity	NPD6033	Approved
0.6885	Remote Similarity	NPD7736	Approved
0.686	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5210	Approved
0.6857	Remote Similarity	NPD4629	Approved
0.6837	Remote Similarity	NPD4221	Approved
0.6837	Remote Similarity	NPD4223	Phase 3
0.6832	Remote Similarity	NPD3573	Approved
0.6822	Remote Similarity	NPD4225	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6804	Remote Similarity	NPD4695	Discontinued
0.6804	Remote Similarity	NPD7525	Registered
0.68	Remote Similarity	NPD5329	Approved
0.6786	Remote Similarity	NPD5128	Approved
0.6786	Remote Similarity	NPD4730	Approved
0.6786	Remote Similarity	NPD4729	Approved
0.6765	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD5737	Approved
0.6765	Remote Similarity	NPD6903	Approved
0.6765	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5279	Phase 3
0.6701	Remote Similarity	NPD7645	Phase 2
0.67	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD4197	Approved
0.6698	Remote Similarity	NPD5695	Phase 3
0.6695	Remote Similarity	NPD7328	Approved
0.6695	Remote Similarity	NPD7327	Approved
0.6695	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD7516	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.6634	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3703	Phase 2
0.661	Remote Similarity	NPD6317	Approved
0.6609	Remote Similarity	NPD5217	Approved
0.6609	Remote Similarity	NPD5216	Approved
0.6609	Remote Similarity	NPD5215	Approved
0.6609	Remote Similarity	NPD5127	Approved
0.6604	Remote Similarity	NPD5282	Discontinued
0.66	Remote Similarity	NPD4788	Approved
0.6598	Remote Similarity	NPD6118	Approved
0.6598	Remote Similarity	NPD6114	Approved
0.6598	Remote Similarity	NPD6697	Approved
0.6598	Remote Similarity	NPD6115	Approved
0.6571	Remote Similarity	NPD5281	Approved
0.6571	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD4138	Approved
0.6569	Remote Similarity	NPD5205	Approved
0.6569	Remote Similarity	NPD4690	Approved
0.6569	Remote Similarity	NPD4689	Approved
0.6569	Remote Similarity	NPD4693	Phase 3
0.6569	Remote Similarity	NPD4519	Discontinued
0.6569	Remote Similarity	NPD4688	Approved
0.6569	Remote Similarity	NPD4623	Approved
0.6555	Remote Similarity	NPD6313	Approved
0.6555	Remote Similarity	NPD6314	Approved
0.6552	Remote Similarity	NPD6053	Discontinued
0.6545	Remote Similarity	NPD5344	Discontinued
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6080	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6529	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD6908	Approved
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6868	Approved
0.6522	Remote Similarity	NPD6371	Approved
0.6495	Remote Similarity	NPD6116	Phase 1
0.6491	Remote Similarity	NPD5168	Approved
0.6489	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD46	Approved
0.6476	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD1694	Approved
0.6452	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6001	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