NPASS Compound

Structure

NPC476415 OpenBabel07101719122D 32 34 0 0 1 0 0 0 0 0999 V2000 3.8228 3.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1498 4.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 3.2609 0.8998 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 -1.8660 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -0.8660 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 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 -0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 3.4659 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 0.8660 1.5000 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 -0.8660 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -4.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3914 1.8912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 6 31 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 18 2 0 0 0 0 14 26 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 32 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 1 0 0 0 20 27 2 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 22 32 1 0 0 0 0 23 25 1 1 0 0 0 24 25 1 1 0 0 0 25 5 1 6 0 0 0 26 17 1 1 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.28
Volume:	474.778
LogP:	3.315
LogD:	2.666
LogS:	-4.587
# Rotatable Bonds:	8
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	4.866
Fsp3:	0.808
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:	-5.346
MDCK Permeability:	6.355269579216838e-05
Pgp-inhibitor:	0.52
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.609

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	94.86502838134766%
Volume Distribution (VD):	0.281
Pgp-substrate:	3.1987502574920654%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.398
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.294
CYP2C9-substrate:	0.557
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.374
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	3.482
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.759
Carcinogencity:	0.321
Eye Corrosion:	0.006
Eye Irritation:	0.275
Respiratory Toxicity:	0.649

Download Data

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

Natural Product: NPC476415

Natural Product ID:	NPC476415
*Common Name:**	Abiesadine U
IUPAC Name:	4-[[(1R,4aR,4bR,7R,10aR)-7-methoxy-1,4a,10a-trimethyl-9-oxo-7-propan-2-yl-3,4,4b,5,6,10-hexahydro-2H-phenanthren-1-yl]methoxy]-4-oxobutanoic acid
Synonyms:
Standard InCHIKey:	NASOHMFLGZORKU-CIHKHTDDSA-N
Standard InCHI:	InChI=1S/C26H40O6/c1-17(2)26(31-6)13-10-19-18(14-26)20(27)15-25(5)23(3,11-7-12-24(19,25)4)16-32-22(30)9-8-21(28)29/h14,17,19H,7-13,15-16H2,1-6H3,(H,28,29)/t19-,23-,24+,25-,26-/m0/s1
SMILES:	CO[C@]1(CC[C@H]2C(=C1)C(=O)C[C@@]1([C@]2(C)CCC[C@@]1(C)COC(=O)CCC(=O)O)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598134
PubChem CID:	46230209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[502215]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[502215]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[502215]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[502215]

☑ 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 NPC476415 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	193
0.1-0.2	1113
0.2-0.3	4065
0.3-0.4	8525
0.4-0.5	13314
0.5-0.6	6910
0.6-0.7	5836
0.7-0.8	2593
0.8-0.85	128
0.85-0.9	15
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC476416
0.9213	High Similarity	NPC476437
0.9213	High Similarity	NPC476369
0.883	High Similarity	NPC170131
0.8681	High Similarity	NPC5509
0.8667	High Similarity	NPC476409
0.8652	High Similarity	NPC30984
0.8652	High Similarity	NPC65661
0.8621	High Similarity	NPC229584
0.8621	High Similarity	NPC14203
0.8621	High Similarity	NPC40228
0.8602	High Similarity	NPC151722
0.8587	High Similarity	NPC159748
0.8587	High Similarity	NPC51486
0.8587	High Similarity	NPC101651
0.8539	High Similarity	NPC476412
0.8495	Intermediate Similarity	NPC472975
0.8485	Intermediate Similarity	NPC118911
0.8478	Intermediate Similarity	NPC477973
0.8478	Intermediate Similarity	NPC168131
0.8478	Intermediate Similarity	NPC174342
0.8478	Intermediate Similarity	NPC284561
0.8444	Intermediate Similarity	NPC189311
0.8444	Intermediate Similarity	NPC86316
0.8444	Intermediate Similarity	NPC106416
0.8438	Intermediate Similarity	NPC474343
0.8438	Intermediate Similarity	NPC253826
0.8409	Intermediate Similarity	NPC278459
0.8404	Intermediate Similarity	NPC169343
0.8387	Intermediate Similarity	NPC198818
0.837	Intermediate Similarity	NPC48107
0.8367	Intermediate Similarity	NPC63249
0.8352	Intermediate Similarity	NPC220478
0.8351	Intermediate Similarity	NPC316598
0.8351	Intermediate Similarity	NPC478056
0.8333	Intermediate Similarity	NPC29952
0.8317	Intermediate Similarity	NPC475294
0.8315	Intermediate Similarity	NPC200513
0.8298	Intermediate Similarity	NPC230064
0.8283	Intermediate Similarity	NPC40918
0.8283	Intermediate Similarity	NPC162973
0.8283	Intermediate Similarity	NPC136289
0.8283	Intermediate Similarity	NPC134077
0.8283	Intermediate Similarity	NPC475320
0.8265	Intermediate Similarity	NPC476274
0.8265	Intermediate Similarity	NPC471413
0.8265	Intermediate Similarity	NPC174314
0.8261	Intermediate Similarity	NPC231599
0.8261	Intermediate Similarity	NPC477228
0.8247	Intermediate Similarity	NPC38530
0.8247	Intermediate Similarity	NPC84335
0.8247	Intermediate Similarity	NPC473456
0.8247	Intermediate Similarity	NPC285513
0.8247	Intermediate Similarity	NPC254496
0.8235	Intermediate Similarity	NPC189075
0.8235	Intermediate Similarity	NPC275539
0.8229	Intermediate Similarity	NPC209355
0.8229	Intermediate Similarity	NPC171395
0.8229	Intermediate Similarity	NPC183012
0.8218	Intermediate Similarity	NPC1679
0.8211	Intermediate Similarity	NPC139692
0.8211	Intermediate Similarity	NPC472871
0.8202	Intermediate Similarity	NPC90055
0.8202	Intermediate Similarity	NPC327002
0.82	Intermediate Similarity	NPC476889
0.82	Intermediate Similarity	NPC478057
0.8191	Intermediate Similarity	NPC214844
0.819	Intermediate Similarity	NPC159333
0.8182	Intermediate Similarity	NPC474327
0.8182	Intermediate Similarity	NPC476888
0.8182	Intermediate Similarity	NPC471412
0.8182	Intermediate Similarity	NPC323441
0.8182	Intermediate Similarity	NPC224720
0.8182	Intermediate Similarity	NPC93744
0.8182	Intermediate Similarity	NPC476223
0.8182	Intermediate Similarity	NPC81530
0.8182	Intermediate Similarity	NPC115862
0.8182	Intermediate Similarity	NPC476240
0.8172	Intermediate Similarity	NPC226863
0.8172	Intermediate Similarity	NPC24816
0.8172	Intermediate Similarity	NPC472870
0.8163	Intermediate Similarity	NPC23364
0.8163	Intermediate Similarity	NPC176845
0.8163	Intermediate Similarity	NPC98868
0.8161	Intermediate Similarity	NPC165711
0.8155	Intermediate Similarity	NPC137911
0.8155	Intermediate Similarity	NPC228477
0.8152	Intermediate Similarity	NPC322159
0.8137	Intermediate Similarity	NPC110496
0.8132	Intermediate Similarity	NPC149869
0.8125	Intermediate Similarity	NPC470697
0.8119	Intermediate Similarity	NPC472868
0.8119	Intermediate Similarity	NPC189616
0.8111	Intermediate Similarity	NPC302661
0.8111	Intermediate Similarity	NPC238991
0.8105	Intermediate Similarity	NPC477783
0.8105	Intermediate Similarity	NPC472814
0.8105	Intermediate Similarity	NPC476417
0.8105	Intermediate Similarity	NPC303697
0.8105	Intermediate Similarity	NPC177037
0.8105	Intermediate Similarity	NPC472978
0.81	Intermediate Similarity	NPC476081
0.81	Intermediate Similarity	NPC476890
0.8095	Intermediate Similarity	NPC475524
0.8095	Intermediate Similarity	NPC100267
0.8085	Intermediate Similarity	NPC469546
0.8085	Intermediate Similarity	NPC262043
0.8085	Intermediate Similarity	NPC472973
0.8081	Intermediate Similarity	NPC117685
0.8081	Intermediate Similarity	NPC54705
0.8077	Intermediate Similarity	NPC473627
0.8077	Intermediate Similarity	NPC37116
0.8068	Intermediate Similarity	NPC321514
0.8068	Intermediate Similarity	NPC198240
0.8065	Intermediate Similarity	NPC136948
0.8061	Intermediate Similarity	NPC121402
0.8061	Intermediate Similarity	NPC151681
0.8061	Intermediate Similarity	NPC204054
0.8061	Intermediate Similarity	NPC476253
0.8061	Intermediate Similarity	NPC107243
0.8061	Intermediate Similarity	NPC224356
0.8061	Intermediate Similarity	NPC132753
0.8061	Intermediate Similarity	NPC57416
0.8061	Intermediate Similarity	NPC76266
0.8061	Intermediate Similarity	NPC175351
0.8061	Intermediate Similarity	NPC257726
0.8043	Intermediate Similarity	NPC474680
0.8043	Intermediate Similarity	NPC2709
0.8043	Intermediate Similarity	NPC476426
0.8041	Intermediate Similarity	NPC134067
0.8041	Intermediate Similarity	NPC295347
0.8041	Intermediate Similarity	NPC139459
0.8041	Intermediate Similarity	NPC274417
0.8041	Intermediate Similarity	NPC293052
0.8022	Intermediate Similarity	NPC102197
0.8022	Intermediate Similarity	NPC49019
0.8022	Intermediate Similarity	NPC22611
0.8021	Intermediate Similarity	NPC166346
0.8021	Intermediate Similarity	NPC474807
0.8021	Intermediate Similarity	NPC115021
0.8021	Intermediate Similarity	NPC472303
0.802	Intermediate Similarity	NPC112009
0.802	Intermediate Similarity	NPC282233
0.802	Intermediate Similarity	NPC236390
0.802	Intermediate Similarity	NPC180204
0.802	Intermediate Similarity	NPC254202
0.802	Intermediate Similarity	NPC95585
0.8019	Intermediate Similarity	NPC25909
0.8019	Intermediate Similarity	NPC471204
0.8	Intermediate Similarity	NPC472643
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC471898
0.8	Intermediate Similarity	NPC471818
0.8	Intermediate Similarity	NPC472866
0.8	Intermediate Similarity	NPC232202
0.8	Intermediate Similarity	NPC472637
0.8	Intermediate Similarity	NPC310981
0.8	Intermediate Similarity	NPC212679
0.8	Intermediate Similarity	NPC220454
0.8	Intermediate Similarity	NPC477782
0.798	Intermediate Similarity	NPC108368
0.798	Intermediate Similarity	NPC222011
0.798	Intermediate Similarity	NPC57079
0.7979	Intermediate Similarity	NPC472302
0.7979	Intermediate Similarity	NPC72397
0.7979	Intermediate Similarity	NPC104560
0.7978	Intermediate Similarity	NPC327674
0.7978	Intermediate Similarity	NPC192999
0.7978	Intermediate Similarity	NPC476438
0.7961	Intermediate Similarity	NPC91034
0.7959	Intermediate Similarity	NPC134072
0.7959	Intermediate Similarity	NPC154526
0.7959	Intermediate Similarity	NPC472363
0.7959	Intermediate Similarity	NPC202833
0.7959	Intermediate Similarity	NPC234993
0.7959	Intermediate Similarity	NPC472362
0.7959	Intermediate Similarity	NPC242848
0.7957	Intermediate Similarity	NPC185638
0.7957	Intermediate Similarity	NPC73038
0.7957	Intermediate Similarity	NPC324063
0.7957	Intermediate Similarity	NPC472869
0.7955	Intermediate Similarity	NPC61952
0.7955	Intermediate Similarity	NPC472300
0.7955	Intermediate Similarity	NPC97377
0.7938	Intermediate Similarity	NPC477129
0.7938	Intermediate Similarity	NPC477130
0.7938	Intermediate Similarity	NPC472977
0.7938	Intermediate Similarity	NPC91010
0.7938	Intermediate Similarity	NPC472976
0.7938	Intermediate Similarity	NPC159410
0.7938	Intermediate Similarity	NPC74751
0.7938	Intermediate Similarity	NPC269729
0.7935	Intermediate Similarity	NPC156981
0.7935	Intermediate Similarity	NPC96095
0.7931	Intermediate Similarity	NPC244166
0.7925	Intermediate Similarity	NPC221144
0.7925	Intermediate Similarity	NPC269530
0.7925	Intermediate Similarity	NPC12046
0.7925	Intermediate Similarity	NPC147180
0.7925	Intermediate Similarity	NPC236217

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 NPC476415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1405
0.2-0.3	3516
0.3-0.4	2550
0.4-0.5	974
0.5-0.6	266
0.6-0.7	152
0.7-0.8	113
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8315	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7902	Approved
0.8211	Intermediate Similarity	NPD6399	Phase 3
0.7938	Intermediate Similarity	NPD7748	Approved
0.7938	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7900	Approved
0.7879	Intermediate Similarity	NPD6084	Phase 2
0.7879	Intermediate Similarity	NPD6083	Phase 2
0.783	Intermediate Similarity	NPD6650	Approved
0.783	Intermediate Similarity	NPD6649	Approved
0.781	Intermediate Similarity	NPD6373	Approved
0.781	Intermediate Similarity	NPD6372	Approved
0.78	Intermediate Similarity	NPD5696	Approved
0.7789	Intermediate Similarity	NPD5737	Approved
0.7789	Intermediate Similarity	NPD6672	Approved
0.7766	Intermediate Similarity	NPD5330	Approved
0.7766	Intermediate Similarity	NPD7521	Approved
0.7766	Intermediate Similarity	NPD7334	Approved
0.7766	Intermediate Similarity	NPD6684	Approved
0.7766	Intermediate Similarity	NPD6409	Approved
0.7766	Intermediate Similarity	NPD7146	Approved
0.7732	Intermediate Similarity	NPD5693	Phase 1
0.7732	Intermediate Similarity	NPD7515	Phase 2
0.7714	Intermediate Similarity	NPD6686	Approved
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD4695	Discontinued
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7684	Intermediate Similarity	NPD3573	Approved
0.7677	Intermediate Similarity	NPD5695	Phase 3
0.766	Intermediate Similarity	NPD1694	Approved
0.7636	Intermediate Similarity	NPD7115	Discovery
0.7624	Intermediate Similarity	NPD7638	Approved
0.7619	Intermediate Similarity	NPD5697	Approved
0.7604	Intermediate Similarity	NPD6903	Approved
0.7604	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.7551	Intermediate Similarity	NPD5281	Approved
0.7551	Intermediate Similarity	NPD5284	Approved
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7526	Intermediate Similarity	NPD6673	Approved
0.7526	Intermediate Similarity	NPD6080	Approved
0.7526	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7453	Intermediate Similarity	NPD5701	Approved
0.7451	Intermediate Similarity	NPD4225	Approved
0.7431	Intermediate Similarity	NPD8297	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7407	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4519	Discontinued
0.7396	Intermediate Similarity	NPD3618	Phase 1
0.7396	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4623	Approved
0.7374	Intermediate Similarity	NPD6079	Approved
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3133	Approved
0.7347	Intermediate Similarity	NPD5328	Approved
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.7347	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4221	Approved
0.734	Intermediate Similarity	NPD4223	Phase 3
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4629	Approved
0.7327	Intermediate Similarity	NPD5210	Approved
0.7292	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD5785	Approved
0.7255	Intermediate Similarity	NPD4697	Phase 3
0.7255	Intermediate Similarity	NPD7614	Phase 1
0.7245	Intermediate Similarity	NPD5208	Approved
0.7238	Intermediate Similarity	NPD5211	Phase 2
0.7216	Intermediate Similarity	NPD6098	Approved
0.7212	Intermediate Similarity	NPD5286	Approved
0.7212	Intermediate Similarity	NPD5285	Approved
0.7212	Intermediate Similarity	NPD4696	Approved
0.72	Intermediate Similarity	NPD6050	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.72	Intermediate Similarity	NPD8035	Phase 2
0.72	Intermediate Similarity	NPD8034	Phase 2
0.7196	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD4197	Approved
0.7188	Intermediate Similarity	NPD4786	Approved
0.7184	Intermediate Similarity	NPD4755	Approved
0.7172	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD3667	Approved
0.7156	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD8039	Approved
0.713	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4202	Approved
0.7117	Intermediate Similarity	NPD6053	Discontinued
0.7105	Intermediate Similarity	NPD6335	Approved
0.7103	Intermediate Similarity	NPD5141	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.71	Intermediate Similarity	NPD5207	Approved
0.7087	Intermediate Similarity	NPD5221	Approved
0.7087	Intermediate Similarity	NPD5222	Approved
0.7087	Intermediate Similarity	NPD7732	Phase 3
0.7087	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6274	Approved
0.7075	Intermediate Similarity	NPD4633	Approved
0.7075	Intermediate Similarity	NPD5225	Approved
0.7075	Intermediate Similarity	NPD5226	Approved
0.7075	Intermediate Similarity	NPD5224	Approved
0.7059	Intermediate Similarity	NPD6001	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7048	Intermediate Similarity	NPD4700	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7041	Intermediate Similarity	NPD5205	Approved
0.7041	Intermediate Similarity	NPD4138	Approved
0.7041	Intermediate Similarity	NPD4689	Approved
0.7041	Intermediate Similarity	NPD4688	Approved
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7041	Intermediate Similarity	NPD4690	Approved
0.7041	Intermediate Similarity	NPD4693	Phase 3
0.7041	Intermediate Similarity	NPD5690	Phase 2
0.703	Intermediate Similarity	NPD5694	Approved
0.7019	Intermediate Similarity	NPD5173	Approved
0.7018	Intermediate Similarity	NPD6317	Approved
0.7009	Intermediate Similarity	NPD5174	Approved
0.7009	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6937	Remote Similarity	NPD6371	Approved
0.6931	Remote Similarity	NPD46	Approved
0.6931	Remote Similarity	NPD6698	Approved
0.693	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7632	Discontinued
0.6915	Remote Similarity	NPD3617	Approved
0.6909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4788	Approved
0.687	Remote Similarity	NPD6009	Approved
0.6869	Remote Similarity	NPD5280	Approved
0.6869	Remote Similarity	NPD4694	Approved
0.6852	Remote Similarity	NPD6052	Approved
0.6852	Remote Similarity	NPD4754	Approved
0.6842	Remote Similarity	NPD4195	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6833	Remote Similarity	NPD7507	Approved
0.6818	Remote Similarity	NPD7331	Phase 2
0.6818	Remote Similarity	NPD6614	Approved
0.6807	Remote Similarity	NPD7604	Phase 2
0.6792	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6909	Approved
0.678	Remote Similarity	NPD5983	Phase 2
0.678	Remote Similarity	NPD6908	Approved
0.6768	Remote Similarity	NPD5363	Approved
0.6757	Remote Similarity	NPD4730	Approved
0.6757	Remote Similarity	NPD4729	Approved
0.6757	Remote Similarity	NPD5128	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6404	Discontinued
0.6727	Remote Similarity	NPD4767	Approved
0.6727	Remote Similarity	NPD4768	Approved
0.6705	Remote Similarity	NPD7341	Phase 2
0.6703	Remote Similarity	NPD4691	Approved
0.67	Remote Similarity	NPD5786	Approved
0.6696	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD7260	Phase 2
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD7078	Approved
0.6637	Remote Similarity	NPD5135	Approved
0.6637	Remote Similarity	NPD5250	Approved
0.6637	Remote Similarity	NPD5248	Approved
0.6637	Remote Similarity	NPD5169	Approved
0.6637	Remote Similarity	NPD5249	Phase 3
0.6637	Remote Similarity	NPD4634	Approved
0.6637	Remote Similarity	NPD5247	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