NPASS Compound

Structure

CID80781 OpenBabel06191715422D 31 33 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 12 25 2 0 0 0 0 12 30 1 0 0 0 0 13 26 2 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 27 2 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 30 1 6 0 0 0 21 22 1 0 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 22 24 1 1 0 0 0 24 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.21
Volume:	443.704
LogP:	4.512
LogD:	2.814
LogS:	-4.109
# Rotatable Bonds:	5
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.356
Synthetic Accessibility Score:	4.279
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	2.6169542252318934e-05
Pgp-inhibitor:	0.775
Pgp-substrate:	0.133
Human Intestinal Absorption (HIA):	0.932
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	95.34908294677734%
Volume Distribution (VD):	1.151
Pgp-substrate:	15.274761199951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.293
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.118
CYP2C9-inhibitor:	0.46
CYP2C9-substrate:	0.661
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	0.975
Half-life (T1/2):	0.32

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.204
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.516
Carcinogencity:	0.046
Eye Corrosion:	0.016
Eye Irritation:	0.872
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC80781

Natural Product ID:	NPC80781
*Common Name:**	IJUVPYONTOHMDC-HYVLGVRCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IJUVPYONTOHMDC-HYVLGVRCSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-11(2)14-17(27)15-16(19(29)18(14)28)24(7)10-8-9-23(5,6)22(24)21(31-13(4)26)20(15)30-12(3)25/h11,20-22,28H,8-10H2,1-7H3/t20-,21+,22-,24+/m0/s1
SMILES:	CC(=O)O[C@H]1C2=C(C(=O)C(=C(C2=O)C(C)C)O)[C@@]2([C@@H]([C@@H]1OC(=O)C)C(C)(C)CCC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2425666
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	twig	n.a.	PMID[22474975]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31347365]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014350]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23300.0	nM	PMID[557096]
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	=	16200.0	nM	PMID[557096]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	15900.0	nM	PMID[557096]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	12100.0	nM	PMID[557096]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	5400.0	nM	PMID[557096]

☑ 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 NPC80781 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	226
0.1-0.2	1400
0.2-0.3	4492
0.3-0.4	8547
0.4-0.5	13787
0.5-0.6	7705
0.6-0.7	5368
0.7-0.8	1140
0.8-0.85	27
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9149	High Similarity	NPC271652
0.8936	High Similarity	NPC113393
0.8723	High Similarity	NPC307298
0.8416	Intermediate Similarity	NPC198880
0.8367	Intermediate Similarity	NPC477436
0.8367	Intermediate Similarity	NPC477435
0.8283	Intermediate Similarity	NPC477439
0.8269	Intermediate Similarity	NPC213366
0.8241	Intermediate Similarity	NPC269530
0.8235	Intermediate Similarity	NPC88198
0.8235	Intermediate Similarity	NPC117685
0.8229	Intermediate Similarity	NPC220930
0.8229	Intermediate Similarity	NPC272039
0.8218	Intermediate Similarity	NPC175351
0.8218	Intermediate Similarity	NPC132753
0.8218	Intermediate Similarity	NPC121402
0.8218	Intermediate Similarity	NPC224356
0.8218	Intermediate Similarity	NPC151681
0.82	Intermediate Similarity	NPC477437
0.82	Intermediate Similarity	NPC477438
0.819	Intermediate Similarity	NPC1679
0.8173	Intermediate Similarity	NPC251017
0.8173	Intermediate Similarity	NPC33973
0.8173	Intermediate Similarity	NPC159533
0.8173	Intermediate Similarity	NPC70967
0.8165	Intermediate Similarity	NPC471204
0.8158	Intermediate Similarity	NPC120724
0.8155	Intermediate Similarity	NPC124211
0.8144	Intermediate Similarity	NPC143025
0.8137	Intermediate Similarity	NPC478056
0.8131	Intermediate Similarity	NPC77947
0.8131	Intermediate Similarity	NPC286174
0.8119	Intermediate Similarity	NPC328162
0.8119	Intermediate Similarity	NPC472362
0.8119	Intermediate Similarity	NPC305483
0.8119	Intermediate Similarity	NPC96859
0.8119	Intermediate Similarity	NPC472363
0.8119	Intermediate Similarity	NPC154526
0.8113	Intermediate Similarity	NPC472925
0.8113	Intermediate Similarity	NPC202524
0.8113	Intermediate Similarity	NPC112780
0.81	Intermediate Similarity	NPC184870
0.81	Intermediate Similarity	NPC470697
0.8095	Intermediate Similarity	NPC470251
0.8095	Intermediate Similarity	NPC135854
0.8095	Intermediate Similarity	NPC2436
0.8095	Intermediate Similarity	NPC216245
0.8091	Intermediate Similarity	NPC284915
0.8081	Intermediate Similarity	NPC248913
0.8077	Intermediate Similarity	NPC119601
0.8077	Intermediate Similarity	NPC53222
0.8077	Intermediate Similarity	NPC295791
0.8077	Intermediate Similarity	NPC137430
0.8077	Intermediate Similarity	NPC308726
0.8073	Intermediate Similarity	NPC476801
0.8061	Intermediate Similarity	NPC280833
0.8058	Intermediate Similarity	NPC157787
0.8058	Intermediate Similarity	NPC476299
0.8058	Intermediate Similarity	NPC476933
0.8058	Intermediate Similarity	NPC474012
0.8056	Intermediate Similarity	NPC272898
0.8056	Intermediate Similarity	NPC129689
0.8056	Intermediate Similarity	NPC470496
0.8056	Intermediate Similarity	NPC473036
0.8039	Intermediate Similarity	NPC121339
0.8037	Intermediate Similarity	NPC89171
0.8037	Intermediate Similarity	NPC476802
0.8037	Intermediate Similarity	NPC476479
0.8037	Intermediate Similarity	NPC151393
0.8036	Intermediate Similarity	NPC240509
0.802	Intermediate Similarity	NPC470016
0.802	Intermediate Similarity	NPC317586
0.8019	Intermediate Similarity	NPC51452
0.8019	Intermediate Similarity	NPC181357
0.8	Intermediate Similarity	NPC105926
0.8	Intermediate Similarity	NPC18945
0.8	Intermediate Similarity	NPC472926
0.8	Intermediate Similarity	NPC472929
0.8	Intermediate Similarity	NPC264048
0.8	Intermediate Similarity	NPC99266
0.8	Intermediate Similarity	NPC8196
0.8	Intermediate Similarity	NPC91693
0.8	Intermediate Similarity	NPC265557
0.7982	Intermediate Similarity	NPC317107
0.7982	Intermediate Similarity	NPC324683
0.7982	Intermediate Similarity	NPC472928
0.7982	Intermediate Similarity	NPC115303
0.7981	Intermediate Similarity	NPC163372
0.7981	Intermediate Similarity	NPC476888
0.7981	Intermediate Similarity	NPC93744
0.7981	Intermediate Similarity	NPC323441
0.7981	Intermediate Similarity	NPC302537
0.7981	Intermediate Similarity	NPC472637
0.7981	Intermediate Similarity	NPC472643
0.798	Intermediate Similarity	NPC472307
0.798	Intermediate Similarity	NPC161638
0.7959	Intermediate Similarity	NPC185059
0.7959	Intermediate Similarity	NPC475001
0.7946	Intermediate Similarity	NPC472927
0.7944	Intermediate Similarity	NPC143609
0.7944	Intermediate Similarity	NPC144854
0.7944	Intermediate Similarity	NPC475294
0.7944	Intermediate Similarity	NPC3316
0.7941	Intermediate Similarity	NPC7124
0.7941	Intermediate Similarity	NPC95565
0.7941	Intermediate Similarity	NPC3772
0.7941	Intermediate Similarity	NPC328371
0.7938	Intermediate Similarity	NPC220478
0.7938	Intermediate Similarity	NPC229717
0.7931	Intermediate Similarity	NPC476729
0.7931	Intermediate Similarity	NPC24651
0.7925	Intermediate Similarity	NPC96268
0.7925	Intermediate Similarity	NPC118911
0.7925	Intermediate Similarity	NPC28656
0.7925	Intermediate Similarity	NPC65523
0.7921	Intermediate Similarity	NPC166906
0.7921	Intermediate Similarity	NPC471720
0.7921	Intermediate Similarity	NPC212812
0.7913	Intermediate Similarity	NPC312833
0.7909	Intermediate Similarity	NPC317687
0.7909	Intermediate Similarity	NPC147180
0.7909	Intermediate Similarity	NPC264634
0.7909	Intermediate Similarity	NPC476163
0.7909	Intermediate Similarity	NPC193948
0.7909	Intermediate Similarity	NPC285956
0.7909	Intermediate Similarity	NPC221144
0.7905	Intermediate Similarity	NPC165250
0.7905	Intermediate Similarity	NPC56498
0.7905	Intermediate Similarity	NPC40918
0.7905	Intermediate Similarity	NPC476890
0.7905	Intermediate Similarity	NPC136289
0.79	Intermediate Similarity	NPC73457
0.789	Intermediate Similarity	NPC473627
0.789	Intermediate Similarity	NPC37116
0.789	Intermediate Similarity	NPC210005
0.7885	Intermediate Similarity	NPC174314
0.7885	Intermediate Similarity	NPC316964
0.7885	Intermediate Similarity	NPC205899
0.7885	Intermediate Similarity	NPC327431
0.7885	Intermediate Similarity	NPC472644
0.7885	Intermediate Similarity	NPC472972
0.7885	Intermediate Similarity	NPC307954
0.7876	Intermediate Similarity	NPC251310
0.7876	Intermediate Similarity	NPC186525
0.7876	Intermediate Similarity	NPC257457
0.7876	Intermediate Similarity	NPC311554
0.787	Intermediate Similarity	NPC192813
0.787	Intermediate Similarity	NPC154608
0.787	Intermediate Similarity	NPC277017
0.787	Intermediate Similarity	NPC475418
0.787	Intermediate Similarity	NPC322903
0.787	Intermediate Similarity	NPC295244
0.787	Intermediate Similarity	NPC318363
0.787	Intermediate Similarity	NPC472439
0.787	Intermediate Similarity	NPC473482
0.787	Intermediate Similarity	NPC275539
0.787	Intermediate Similarity	NPC469916
0.787	Intermediate Similarity	NPC189075
0.7864	Intermediate Similarity	NPC106557
0.7864	Intermediate Similarity	NPC43747
0.7864	Intermediate Similarity	NPC254496
0.7864	Intermediate Similarity	NPC84335
0.7864	Intermediate Similarity	NPC73911
0.7864	Intermediate Similarity	NPC285513
0.7864	Intermediate Similarity	NPC18319
0.7864	Intermediate Similarity	NPC216904
0.7864	Intermediate Similarity	NPC38530
0.7864	Intermediate Similarity	NPC474343
0.7857	Intermediate Similarity	NPC16081
0.7857	Intermediate Similarity	NPC173686
0.7857	Intermediate Similarity	NPC64318
0.7857	Intermediate Similarity	NPC478216
0.785	Intermediate Similarity	NPC478052
0.785	Intermediate Similarity	NPC472645
0.785	Intermediate Similarity	NPC469607
0.785	Intermediate Similarity	NPC111952
0.785	Intermediate Similarity	NPC477125
0.7845	Intermediate Similarity	NPC67251
0.7843	Intermediate Similarity	NPC469995
0.7843	Intermediate Similarity	NPC473648
0.7843	Intermediate Similarity	NPC183012
0.7843	Intermediate Similarity	NPC37646
0.7843	Intermediate Similarity	NPC174948
0.7843	Intermediate Similarity	NPC295347
0.7843	Intermediate Similarity	NPC173875
0.7843	Intermediate Similarity	NPC255809
0.7843	Intermediate Similarity	NPC318282
0.7838	Intermediate Similarity	NPC33360
0.7838	Intermediate Similarity	NPC198539
0.7838	Intermediate Similarity	NPC159333
0.783	Intermediate Similarity	NPC275583
0.783	Intermediate Similarity	NPC471208
0.783	Intermediate Similarity	NPC55872
0.783	Intermediate Similarity	NPC95899
0.783	Intermediate Similarity	NPC476889
0.783	Intermediate Similarity	NPC90177
0.783	Intermediate Similarity	NPC179208
0.783	Intermediate Similarity	NPC159442
0.7822	Intermediate Similarity	NPC470254
0.7818	Intermediate Similarity	NPC34315

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 NPC80781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1770
0.2-0.3	3623
0.3-0.4	2225
0.4-0.5	863
0.5-0.6	255
0.6-0.7	187
0.7-0.8	10
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
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD4225	Approved
0.7573	Intermediate Similarity	NPD7748	Approved
0.7545	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7902	Approved
0.7523	Intermediate Similarity	NPD6402	Approved
0.7523	Intermediate Similarity	NPD7128	Approved
0.7523	Intermediate Similarity	NPD5739	Approved
0.7523	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7434	Intermediate Similarity	NPD8297	Approved
0.7411	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6899	Approved
0.7387	Intermediate Similarity	NPD6881	Approved
0.7387	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD6411	Approved
0.7379	Intermediate Similarity	NPD7515	Phase 2
0.7353	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6649	Approved
0.7345	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6399	Phase 3
0.73	Intermediate Similarity	NPD1694	Approved
0.7297	Intermediate Similarity	NPD5701	Approved
0.7297	Intermediate Similarity	NPD5697	Approved
0.729	Intermediate Similarity	NPD7638	Approved
0.7264	Intermediate Similarity	NPD4697	Phase 3
0.7257	Intermediate Similarity	NPD6883	Approved
0.7257	Intermediate Similarity	NPD7102	Approved
0.7257	Intermediate Similarity	NPD7290	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3
0.7238	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7900	Approved
0.7232	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.7193	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7193	Intermediate Similarity	NPD6847	Approved
0.7193	Intermediate Similarity	NPD6869	Approved
0.7193	Intermediate Similarity	NPD6617	Approved
0.7184	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6101	Approved
0.7184	Intermediate Similarity	NPD5328	Approved
0.717	Intermediate Similarity	NPD5695	Phase 3
0.7168	Intermediate Similarity	NPD6012	Approved
0.7168	Intermediate Similarity	NPD6013	Approved
0.7168	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.712	Intermediate Similarity	NPD7260	Phase 2
0.7103	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5222	Approved
0.7103	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD6672	Approved
0.7087	Intermediate Similarity	NPD5737	Approved
0.7069	Intermediate Similarity	NPD4632	Approved
0.7063	Intermediate Similarity	NPD6845	Suspended
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7049	Intermediate Similarity	NPD7492	Approved
0.7048	Intermediate Similarity	NPD6079	Approved
0.7037	Intermediate Similarity	NPD5173	Approved
0.7037	Intermediate Similarity	NPD4755	Approved
0.7037	Intermediate Similarity	NPD6083	Phase 2
0.7037	Intermediate Similarity	NPD6084	Phase 2
0.7018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.699	Remote Similarity	NPD3573	Approved
0.6972	Remote Similarity	NPD5696	Approved
0.697	Remote Similarity	NPD4695	Discontinued
0.6949	Remote Similarity	NPD6868	Approved
0.6939	Remote Similarity	NPD3617	Approved
0.6937	Remote Similarity	NPD5211	Phase 2
0.6935	Remote Similarity	NPD8293	Discontinued
0.6935	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD4696	Approved
0.6909	Remote Similarity	NPD5286	Approved
0.6909	Remote Similarity	NPD5285	Approved
0.6909	Remote Similarity	NPD4700	Approved
0.6903	Remote Similarity	NPD6008	Approved
0.6893	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6409	Approved
0.6893	Remote Similarity	NPD7521	Approved
0.6893	Remote Similarity	NPD7334	Approved
0.6893	Remote Similarity	NPD5330	Approved
0.6893	Remote Similarity	NPD7146	Approved
0.6893	Remote Similarity	NPD6684	Approved
0.6891	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD5693	Phase 1
0.6885	Remote Similarity	NPD6370	Approved
0.688	Remote Similarity	NPD7736	Approved
0.6852	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5223	Approved
0.6833	Remote Similarity	NPD6335	Approved
0.6832	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7604	Phase 2
0.6825	Remote Similarity	NPD7319	Approved
0.6814	Remote Similarity	NPD5141	Approved
0.681	Remote Similarity	NPD4634	Approved
0.6807	Remote Similarity	NPD6274	Approved
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD6921	Approved
0.6803	Remote Similarity	NPD5983	Phase 2
0.6803	Remote Similarity	NPD6015	Approved
0.6792	Remote Similarity	NPD5785	Approved
0.6786	Remote Similarity	NPD5226	Approved
0.6786	Remote Similarity	NPD4633	Approved
0.6786	Remote Similarity	NPD5225	Approved
0.6786	Remote Similarity	NPD5224	Approved
0.6783	Remote Similarity	NPD6686	Approved
0.6777	Remote Similarity	NPD7101	Approved
0.6777	Remote Similarity	NPD7100	Approved
0.6762	Remote Similarity	NPD6903	Approved
0.6762	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6317	Approved
0.6748	Remote Similarity	NPD5988	Approved
0.6731	Remote Similarity	NPD5279	Phase 3
0.6729	Remote Similarity	NPD6050	Approved
0.6729	Remote Similarity	NPD8034	Phase 2
0.6729	Remote Similarity	NPD8035	Phase 2
0.6726	Remote Similarity	NPD5175	Approved
0.6726	Remote Similarity	NPD5174	Approved
0.6726	Remote Similarity	NPD4754	Approved
0.672	Remote Similarity	NPD6336	Discontinued
0.672	Remote Similarity	NPD7507	Approved
0.6699	Remote Similarity	NPD4786	Approved
0.6698	Remote Similarity	NPD6080	Approved
0.6698	Remote Similarity	NPD6673	Approved
0.6698	Remote Similarity	NPD6904	Approved
0.6697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6053	Discontinued
0.6694	Remote Similarity	NPD6314	Approved
0.6694	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD5692	Phase 3
0.6614	Remote Similarity	NPD6033	Approved
0.6609	Remote Similarity	NPD4767	Approved
0.6609	Remote Similarity	NPD4768	Approved
0.6574	Remote Similarity	NPD5281	Approved
0.6574	Remote Similarity	NPD5284	Approved
0.6574	Remote Similarity	NPD5694	Approved
0.6552	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4753	Phase 2
0.6538	Remote Similarity	NPD3665	Phase 1
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6532	Remote Similarity	NPD8517	Approved
0.6532	Remote Similarity	NPD8516	Approved
0.6532	Remote Similarity	NPD8513	Phase 3
0.6532	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD6371	Approved
0.6514	Remote Similarity	NPD4202	Approved
0.6496	Remote Similarity	NPD4729	Approved
0.6496	Remote Similarity	NPD4730	Approved
0.6496	Remote Similarity	NPD5168	Approved
0.6496	Remote Similarity	NPD5128	Approved
0.6486	Remote Similarity	NPD7614	Phase 1
0.6481	Remote Similarity	NPD46	Approved
0.6481	Remote Similarity	NPD6698	Approved
0.6476	Remote Similarity	NPD5329	Approved
0.6476	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5282	Discontinued
0.6415	Remote Similarity	NPD5280	Approved
0.6415	Remote Similarity	NPD5690	Phase 2
0.6415	Remote Similarity	NPD5786	Approved
0.6415	Remote Similarity	NPD4694	Approved
0.6415	Remote Similarity	NPD6098	Approved
0.641	Remote Similarity	NPD6412	Phase 2
0.6396	Remote Similarity	NPD5654	Approved
0.6396	Remote Similarity	NPD5210	Approved
0.6396	Remote Similarity	NPD4629	Approved
0.6387	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5135	Approved
0.6387	Remote Similarity	NPD5248	Approved
0.6387	Remote Similarity	NPD5251	Approved
0.6387	Remote Similarity	NPD5169	Approved
0.6387	Remote Similarity	NPD5247	Approved
0.6387	Remote Similarity	NPD5249	Phase 3
0.6387	Remote Similarity	NPD5250	Approved
0.6381	Remote Similarity	NPD4197	Approved
0.6381	Remote Similarity	NPD3668	Phase 3
0.6339	Remote Similarity	NPD7732	Phase 3
0.6333	Remote Similarity	NPD5127	Approved
0.6333	Remote Similarity	NPD5215	Approved
0.6333	Remote Similarity	NPD5216	Approved
0.6333	Remote Similarity	NPD5217	Approved
0.633	Remote Similarity	NPD5207	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