NPASS Compound

Structure

NPC293086 OpenBabel07101718232D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.3950 -1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1270 1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6270 2.2314 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 -8.8591 0.3653 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 -6.1270 -1.6347 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 -6.9931 -1.1347 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 -6.9931 1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8591 1.3653 0.0000 C 0 0 0 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 -5.2610 -0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9931 -0.1347 0.0000 C 0 0 1 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 0 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 -6.1270 0.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1270 1.3653 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 -7.8591 0.3653 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 0.2314 -2.6478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3591 -0.5007 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 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 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 6 0 0 0 19 20 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 6 0 0 0 22 30 1 0 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 28 1 6 0 0 0 24 34 1 0 0 0 0 25 20 1 6 0 0 0 25 26 1 0 0 0 0 27 34 1 0 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 29 32 1 0 0 0 0 30 8 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	523.098
LogP:	5.666
LogD:	4.19
LogS:	-4.729
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.31
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.649
MDCK Permeability:	1.6722453437978402e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.768
Plasma Protein Binding (PPB):	87.8561782836914%
Volume Distribution (VD):	1.031
Pgp-substrate:	2.7271649837493896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.74

ADMET: Excretion

Clearance (CL):	9.852
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.621
Carcinogencity:	0.425
Eye Corrosion:	0.063
Eye Irritation:	0.03
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC293086

Natural Product ID:	NPC293086
*Common Name:**	(5As,6S,7S,9As)-7-Hydroxy-6-((E)-2-((2R,4As,5S,8Ar)-5-Hydroxy-2,5,8,8-Tetramethyloctahydronaphthalen-1(2H)-Ylidene)-Ethyl)-2,2,5A,7-Tetramethyloctahydrobenzo(B)Oxepin-3(2H)-One
IUPAC Name:	(5aS,6S,7S,9aS)-6-[(2E)-2-[(2R,4aS,5S,8aR)-5-hydroxy-2,5,8,8-tetramethyl-3,4,4a,6,7,8a-hexahydro-2H-naphthalen-1-ylidene]ethyl]-7-hydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydrobenzo[b]oxepin-3-one
Synonyms:
Standard InCHIKey:	DPIZIYOJDMMKNP-GKMAIPHXSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-19-9-11-21-25(26(2,3)17-18-29(21,7)32)20(19)10-12-22-28(6)15-13-23(31)27(4,5)34-24(28)14-16-30(22,8)33/h10,19,21-22,24-25,32-33H,9,11-18H2,1-8H3/b20-10+/t19-,21+,22+,24+,25-,28+,29+,30+/m1/s1
SMILES:	C[C@@H]1CC[C@H]2[C@@H](/C/1=C/C[C@@H]1[C@@](C)(O)CC[C@H]3[C@@]1(C)CCC(=O)C(O3)(C)C)C(C)(C)CC[C@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561532
PubChem CID:	44234695
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	=	0.8	n.a.	PMID[451672]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	11.0	n.a.	PMID[451672]

☑ 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 NPC293086 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	217
0.1-0.2	1464
0.2-0.3	5400
0.3-0.4	12735
0.4-0.5	10437
0.5-0.6	6140
0.6-0.7	5095
0.7-0.8	1188
0.8-0.85	16
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8913	High Similarity	NPC212812
0.8696	High Similarity	NPC248913
0.8632	High Similarity	NPC272451
0.8632	High Similarity	NPC470834
0.8571	High Similarity	NPC194323
0.8384	Intermediate Similarity	NPC90177
0.8315	Intermediate Similarity	NPC48362
0.8283	Intermediate Similarity	NPC470840
0.8265	Intermediate Similarity	NPC46761
0.82	Intermediate Similarity	NPC179208
0.82	Intermediate Similarity	NPC470839
0.8172	Intermediate Similarity	NPC475001
0.8172	Intermediate Similarity	NPC185059
0.8152	Intermediate Similarity	NPC34190
0.8152	Intermediate Similarity	NPC73038
0.8144	Intermediate Similarity	NPC157113
0.8144	Intermediate Similarity	NPC62516
0.8132	Intermediate Similarity	NPC251170
0.8125	Intermediate Similarity	NPC272635
0.8125	Intermediate Similarity	NPC103527
0.8125	Intermediate Similarity	NPC169751
0.8125	Intermediate Similarity	NPC477439
0.8119	Intermediate Similarity	NPC40170
0.8105	Intermediate Similarity	NPC474525
0.8105	Intermediate Similarity	NPC185936
0.8105	Intermediate Similarity	NPC168027
0.8085	Intermediate Similarity	NPC69627
0.8085	Intermediate Similarity	NPC474245
0.8081	Intermediate Similarity	NPC472972
0.8081	Intermediate Similarity	NPC15390
0.8061	Intermediate Similarity	NPC473456
0.8061	Intermediate Similarity	NPC18509
0.8043	Intermediate Similarity	NPC133954
0.8041	Intermediate Similarity	NPC477438
0.8041	Intermediate Similarity	NPC139570
0.8041	Intermediate Similarity	NPC477437
0.8041	Intermediate Similarity	NPC134067
0.8021	Intermediate Similarity	NPC477435
0.8021	Intermediate Similarity	NPC477436
0.8	Intermediate Similarity	NPC120840
0.8	Intermediate Similarity	NPC474728
0.8	Intermediate Similarity	NPC473217
0.8	Intermediate Similarity	NPC46441
0.8	Intermediate Similarity	NPC113989
0.798	Intermediate Similarity	NPC260149
0.798	Intermediate Similarity	NPC58942
0.7979	Intermediate Similarity	NPC193360
0.7979	Intermediate Similarity	NPC472802
0.7961	Intermediate Similarity	NPC44063
0.7959	Intermediate Similarity	NPC327179
0.7959	Intermediate Similarity	NPC91439
0.7959	Intermediate Similarity	NPC260223
0.7959	Intermediate Similarity	NPC219353
0.7957	Intermediate Similarity	NPC325594
0.7957	Intermediate Similarity	NPC213412
0.7957	Intermediate Similarity	NPC74363
0.7957	Intermediate Similarity	NPC475862
0.7941	Intermediate Similarity	NPC137657
0.7941	Intermediate Similarity	NPC284865
0.7941	Intermediate Similarity	NPC29705
0.7938	Intermediate Similarity	NPC23170
0.7938	Intermediate Similarity	NPC474529
0.7938	Intermediate Similarity	NPC160413
0.7938	Intermediate Similarity	NPC74751
0.7935	Intermediate Similarity	NPC156981
0.7917	Intermediate Similarity	NPC472978
0.7917	Intermediate Similarity	NPC472975
0.7917	Intermediate Similarity	NPC470590
0.7917	Intermediate Similarity	NPC60755
0.7917	Intermediate Similarity	NPC105189
0.7917	Intermediate Similarity	NPC77099
0.7917	Intermediate Similarity	NPC285184
0.7917	Intermediate Similarity	NPC99380
0.7912	Intermediate Similarity	NPC163236
0.79	Intermediate Similarity	NPC144956
0.7895	Intermediate Similarity	NPC30522
0.7895	Intermediate Similarity	NPC25906
0.7895	Intermediate Similarity	NPC290972
0.7895	Intermediate Similarity	NPC472973
0.7895	Intermediate Similarity	NPC64872
0.7885	Intermediate Similarity	NPC94529
0.7879	Intermediate Similarity	NPC190554
0.7879	Intermediate Similarity	NPC254496
0.7879	Intermediate Similarity	NPC285513
0.7872	Intermediate Similarity	NPC73064
0.7864	Intermediate Similarity	NPC85529
0.7864	Intermediate Similarity	NPC32006
0.7857	Intermediate Similarity	NPC473240
0.7857	Intermediate Similarity	NPC272617
0.7857	Intermediate Similarity	NPC279974
0.7857	Intermediate Similarity	NPC473170
0.785	Intermediate Similarity	NPC477266
0.7841	Intermediate Similarity	NPC167873
0.7841	Intermediate Similarity	NPC1973
0.7835	Intermediate Similarity	NPC158059
0.7835	Intermediate Similarity	NPC86368
0.7835	Intermediate Similarity	NPC118519
0.7835	Intermediate Similarity	NPC295643
0.7835	Intermediate Similarity	NPC118490
0.7835	Intermediate Similarity	NPC272075
0.7835	Intermediate Similarity	NPC214756
0.7835	Intermediate Similarity	NPC202728
0.7835	Intermediate Similarity	NPC12722
0.7826	Intermediate Similarity	NPC64600
0.7822	Intermediate Similarity	NPC477053
0.7822	Intermediate Similarity	NPC118964
0.7822	Intermediate Similarity	NPC477052
0.7822	Intermediate Similarity	NPC477051
0.7812	Intermediate Similarity	NPC477872
0.7812	Intermediate Similarity	NPC120968
0.7812	Intermediate Similarity	NPC471896
0.7812	Intermediate Similarity	NPC134321
0.7812	Intermediate Similarity	NPC7260
0.7812	Intermediate Similarity	NPC273621
0.7812	Intermediate Similarity	NPC18872
0.7812	Intermediate Similarity	NPC475823
0.7812	Intermediate Similarity	NPC227467
0.7812	Intermediate Similarity	NPC210037
0.7812	Intermediate Similarity	NPC128672
0.7812	Intermediate Similarity	NPC223093
0.7812	Intermediate Similarity	NPC193750
0.7812	Intermediate Similarity	NPC474209
0.7812	Intermediate Similarity	NPC290614
0.7812	Intermediate Similarity	NPC291028
0.7812	Intermediate Similarity	NPC130278
0.781	Intermediate Similarity	NPC2766
0.7802	Intermediate Similarity	NPC328264
0.78	Intermediate Similarity	NPC191565
0.78	Intermediate Similarity	NPC17183
0.7789	Intermediate Similarity	NPC52169
0.7789	Intermediate Similarity	NPC230387
0.7789	Intermediate Similarity	NPC246708
0.7789	Intermediate Similarity	NPC182797
0.7789	Intermediate Similarity	NPC328539
0.7789	Intermediate Similarity	NPC474925
0.7789	Intermediate Similarity	NPC40552
0.7788	Intermediate Similarity	NPC473169
0.7778	Intermediate Similarity	NPC160056
0.7778	Intermediate Similarity	NPC49371
0.7778	Intermediate Similarity	NPC476318
0.7778	Intermediate Similarity	NPC61369
0.7778	Intermediate Similarity	NPC469545
0.7778	Intermediate Similarity	NPC471039
0.7778	Intermediate Similarity	NPC5532
0.7778	Intermediate Similarity	NPC476327
0.7778	Intermediate Similarity	NPC192428
0.7778	Intermediate Similarity	NPC165616
0.7766	Intermediate Similarity	NPC95594
0.7766	Intermediate Similarity	NPC158393
0.7766	Intermediate Similarity	NPC477579
0.7766	Intermediate Similarity	NPC51014
0.7766	Intermediate Similarity	NPC20688
0.7766	Intermediate Similarity	NPC235341
0.7757	Intermediate Similarity	NPC474516
0.7755	Intermediate Similarity	NPC296164
0.7755	Intermediate Similarity	NPC114159
0.7755	Intermediate Similarity	NPC184006
0.7755	Intermediate Similarity	NPC471040
0.7755	Intermediate Similarity	NPC472976
0.7755	Intermediate Similarity	NPC245972
0.7755	Intermediate Similarity	NPC6818
0.7755	Intermediate Similarity	NPC196485
0.7755	Intermediate Similarity	NPC191412
0.7755	Intermediate Similarity	NPC472977
0.7755	Intermediate Similarity	NPC159410
0.7755	Intermediate Similarity	NPC78580
0.7755	Intermediate Similarity	NPC471207
0.7755	Intermediate Similarity	NPC23621
0.7753	Intermediate Similarity	NPC472746
0.7745	Intermediate Similarity	NPC162973
0.7745	Intermediate Similarity	NPC136289
0.7745	Intermediate Similarity	NPC477054
0.7742	Intermediate Similarity	NPC180834
0.7742	Intermediate Similarity	NPC227132
0.7732	Intermediate Similarity	NPC473166
0.7732	Intermediate Similarity	NPC38754
0.7732	Intermediate Similarity	NPC198054
0.7732	Intermediate Similarity	NPC327515
0.7732	Intermediate Similarity	NPC187722
0.7732	Intermediate Similarity	NPC145067
0.7732	Intermediate Similarity	NPC233455
0.7732	Intermediate Similarity	NPC4036
0.7732	Intermediate Similarity	NPC158030
0.7732	Intermediate Similarity	NPC65120
0.7732	Intermediate Similarity	NPC473167
0.7727	Intermediate Similarity	NPC318751
0.7723	Intermediate Similarity	NPC293890
0.7723	Intermediate Similarity	NPC474802
0.7723	Intermediate Similarity	NPC117685
0.7723	Intermediate Similarity	NPC83709
0.7714	Intermediate Similarity	NPC153587
0.7708	Intermediate Similarity	NPC127689
0.7708	Intermediate Similarity	NPC61543
0.7708	Intermediate Similarity	NPC130520
0.7708	Intermediate Similarity	NPC263393
0.7708	Intermediate Similarity	NPC198664
0.7708	Intermediate Similarity	NPC225585
0.7708	Intermediate Similarity	NPC229871
0.7708	Intermediate Similarity	NPC275740
0.7708	Intermediate Similarity	NPC234346

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 NPC293086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1768
0.2-0.3	4023
0.3-0.4	2136
0.4-0.5	612
0.5-0.6	191
0.6-0.7	147
0.7-0.8	74
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
0.8218	Intermediate Similarity	NPD6675	Approved
0.8218	Intermediate Similarity	NPD5739	Approved
0.8218	Intermediate Similarity	NPD7128	Approved
0.8218	Intermediate Similarity	NPD6402	Approved
0.8061	Intermediate Similarity	NPD4755	Approved
0.8058	Intermediate Similarity	NPD6881	Approved
0.8058	Intermediate Similarity	NPD7320	Approved
0.8058	Intermediate Similarity	NPD6899	Approved
0.7981	Intermediate Similarity	NPD6372	Approved
0.7981	Intermediate Similarity	NPD6373	Approved
0.7961	Intermediate Similarity	NPD5701	Approved
0.7961	Intermediate Similarity	NPD5697	Approved
0.7938	Intermediate Similarity	NPD7748	Approved
0.7905	Intermediate Similarity	NPD6883	Approved
0.7905	Intermediate Similarity	NPD7290	Approved
0.7905	Intermediate Similarity	NPD7102	Approved
0.79	Intermediate Similarity	NPD5286	Approved
0.79	Intermediate Similarity	NPD4700	Approved
0.79	Intermediate Similarity	NPD4696	Approved
0.79	Intermediate Similarity	NPD5285	Approved
0.7895	Intermediate Similarity	NPD5328	Approved
0.7885	Intermediate Similarity	NPD6011	Approved
0.7879	Intermediate Similarity	NPD7902	Approved
0.783	Intermediate Similarity	NPD6650	Approved
0.783	Intermediate Similarity	NPD6617	Approved
0.783	Intermediate Similarity	NPD6649	Approved
0.783	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD6869	Approved
0.783	Intermediate Similarity	NPD8130	Phase 1
0.783	Intermediate Similarity	NPD6847	Approved
0.7822	Intermediate Similarity	NPD5223	Approved
0.781	Intermediate Similarity	NPD6013	Approved
0.781	Intermediate Similarity	NPD6012	Approved
0.781	Intermediate Similarity	NPD6014	Approved
0.7778	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5221	Approved
0.7778	Intermediate Similarity	NPD5222	Approved
0.7757	Intermediate Similarity	NPD6882	Approved
0.7757	Intermediate Similarity	NPD8297	Approved
0.7745	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD4633	Approved
0.7745	Intermediate Similarity	NPD5224	Approved
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD5226	Approved
0.7732	Intermediate Similarity	NPD6079	Approved
0.7732	Intermediate Similarity	NPD7515	Phase 2
0.77	Intermediate Similarity	NPD5173	Approved
0.767	Intermediate Similarity	NPD5175	Approved
0.767	Intermediate Similarity	NPD4754	Approved
0.767	Intermediate Similarity	NPD5174	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.7596	Intermediate Similarity	NPD5141	Approved
0.7579	Intermediate Similarity	NPD3618	Phase 1
0.7576	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7900	Approved
0.7553	Intermediate Similarity	NPD4786	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7525	Intermediate Similarity	NPD6084	Phase 2
0.7525	Intermediate Similarity	NPD6083	Phase 2
0.7524	Intermediate Similarity	NPD4767	Approved
0.7524	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7475	Intermediate Similarity	NPD4202	Approved
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6672	Approved
0.7411	Intermediate Similarity	NPD6335	Approved
0.7387	Intermediate Similarity	NPD6274	Approved
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD5128	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.7345	Intermediate Similarity	NPD7101	Approved
0.7345	Intermediate Similarity	NPD7100	Approved
0.7327	Intermediate Similarity	NPD5695	Phase 3
0.7321	Intermediate Similarity	NPD6317	Approved
0.732	Intermediate Similarity	NPD3573	Approved
0.7312	Intermediate Similarity	NPD4695	Discontinued
0.7292	Intermediate Similarity	NPD5329	Approved
0.7282	Intermediate Similarity	NPD5696	Approved
0.7281	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD6054	Approved
0.7257	Intermediate Similarity	NPD6313	Approved
0.7257	Intermediate Similarity	NPD6314	Approved
0.7248	Intermediate Similarity	NPD5169	Approved
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7248	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4634	Approved
0.7248	Intermediate Similarity	NPD5135	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5248	Approved
0.7232	Intermediate Similarity	NPD6868	Approved
0.7222	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6908	Approved
0.7217	Intermediate Similarity	NPD6909	Approved
0.7216	Intermediate Similarity	NPD6098	Approved
0.7207	Intermediate Similarity	NPD4632	Approved
0.7204	Intermediate Similarity	NPD7645	Phase 2
0.7188	Intermediate Similarity	NPD4197	Approved
0.7188	Intermediate Similarity	NPD3133	Approved
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7188	Intermediate Similarity	NPD3665	Phase 1
0.7188	Intermediate Similarity	NPD3666	Approved
0.7182	Intermediate Similarity	NPD5217	Approved
0.7182	Intermediate Similarity	NPD5127	Approved
0.7182	Intermediate Similarity	NPD5216	Approved
0.7182	Intermediate Similarity	NPD5215	Approved
0.7172	Intermediate Similarity	NPD6904	Approved
0.7172	Intermediate Similarity	NPD6673	Approved
0.7172	Intermediate Similarity	NPD6080	Approved
0.7168	Intermediate Similarity	NPD6009	Approved
0.7155	Intermediate Similarity	NPD6370	Approved
0.713	Intermediate Similarity	NPD6319	Approved
0.7115	Intermediate Similarity	NPD7638	Approved
0.7113	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7094	Intermediate Similarity	NPD7604	Phase 2
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6015	Approved
0.7069	Intermediate Similarity	NPD6016	Approved
0.7069	Intermediate Similarity	NPD5983	Phase 2
0.7064	Intermediate Similarity	NPD5168	Approved
0.7048	Intermediate Similarity	NPD7639	Approved
0.7048	Intermediate Similarity	NPD7640	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7037	Intermediate Similarity	NPD6008	Approved
0.7034	Intermediate Similarity	NPD7492	Approved
0.703	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD5988	Approved
0.7	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD5167	Approved
0.699	Remote Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5210	Approved
0.6979	Remote Similarity	NPD4223	Phase 3
0.6979	Remote Similarity	NPD4221	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.6975	Remote Similarity	NPD6336	Discontinued
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8293	Discontinued
0.6917	Remote Similarity	NPD7078	Approved
0.6915	Remote Similarity	NPD3617	Approved
0.6907	Remote Similarity	NPD4788	Approved
0.69	Remote Similarity	NPD6903	Approved
0.687	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5280	Approved
0.6869	Remote Similarity	NPD4694	Approved
0.6869	Remote Similarity	NPD5690	Phase 2
0.6863	Remote Similarity	NPD6050	Approved
0.6863	Remote Similarity	NPD5693	Phase 1
0.686	Remote Similarity	NPD6033	Approved
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3703	Phase 2
0.6765	Remote Similarity	NPD5692	Phase 3
0.67	Remote Similarity	NPD4689	Approved
0.67	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD4693	Phase 3
0.67	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD4688	Approved
0.67	Remote Similarity	NPD4138	Approved
0.67	Remote Similarity	NPD4623	Approved
0.67	Remote Similarity	NPD4690	Approved
0.6699	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6632	Remote Similarity	NPD6116	Phase 1
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7339	Approved
0.6596	Remote Similarity	NPD6942	Approved
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD5282	Discontinued
0.6557	Remote Similarity	NPD7507	Approved
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5284	Approved
0.6538	Remote Similarity	NPD5281	Approved
0.6526	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6117	Approved
0.6522	Remote Similarity	NPD4789	Approved
0.65	Remote Similarity	NPD6921	Approved
0.6491	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5360	Phase 3
0.6484	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5779	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