NPASS Compound

Structure

NPC476416 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 -0.6340 4.8301 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 1 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 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 0.3660 4.8301 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 17 26 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 31 1 0 0 0 0 22 29 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 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.28
Volume:	474.778
LogP:	3.514
LogD:	3.22
LogS:	-4.852
# 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:	0.607
Synthetic Accessibility Score:	4.766
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:	-4.926
MDCK Permeability:	6.712986214552075e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.668
30% Bioavailability (F30%):	0.846

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.82
Plasma Protein Binding (PPB):	83.52133178710938%
Volume Distribution (VD):	0.351
Pgp-substrate:	14.724296569824219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.436
CYP2C19-inhibitor:	0.304
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.719

ADMET: Excretion

Clearance (CL):	4.906
Half-life (T1/2):	0.543

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.89
Carcinogencity:	0.501
Eye Corrosion:	0.009
Eye Irritation:	0.137
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC476416

Natural Product ID:	NPC476416
*Common Name:**	Abiesadine V
IUPAC Name:	4-O-[[(1R,4aR,4bR,7S,10aR)-7-hydroxy-1,4a,10a-trimethyl-9-oxo-7-propan-2-yl-3,4,4b,5,6,10-hexahydro-2H-phenanthren-1-yl]methyl] 1-O-methyl butanedioate
Synonyms:
Standard InCHIKey:	AHBQIYSLXQMIEO-WBZPMCRCSA-N
Standard InCHI:	InChI=1S/C26H40O6/c1-17(2)26(30)13-10-19-18(14-26)20(27)15-25(5)23(3,11-7-12-24(19,25)4)16-32-22(29)9-8-21(28)31-6/h14,17,19,30H,7-13,15-16H2,1-6H3/t19-,23-,24+,25-,26+/m0/s1
SMILES:	CC(C)C1(CCC2C(=C1)C(=O)CC3(C2(CCCC3(C)COC(=O)CCC(=O)OC)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598135
PubChem CID:	46230210
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	=	56.8	ug.mL-1	PMID[509903]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[509903]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[509903]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[509903]

☑ 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 NPC476416 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	191
0.1-0.2	1074
0.2-0.3	4232
0.3-0.4	8857
0.4-0.5	13097
0.5-0.6	6931
0.6-0.7	5596
0.7-0.8	2543
0.8-0.85	156
0.85-0.9	17
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC476415
0.913	High Similarity	NPC170131
0.8977	High Similarity	NPC476409
0.8901	High Similarity	NPC151722
0.8889	High Similarity	NPC476437
0.8889	High Similarity	NPC476369
0.8851	High Similarity	NPC476412
0.8667	High Similarity	NPC48107
0.8632	High Similarity	NPC478056
0.8571	High Similarity	NPC477973
0.8557	High Similarity	NPC136289
0.8542	High Similarity	NPC476274
0.8506	High Similarity	NPC278459
0.8478	Intermediate Similarity	NPC214844
0.8469	Intermediate Similarity	NPC478057
0.8462	Intermediate Similarity	NPC472870
0.8454	Intermediate Similarity	NPC224720
0.8454	Intermediate Similarity	NPC81530
0.8454	Intermediate Similarity	NPC115862
0.8454	Intermediate Similarity	NPC476240
0.8454	Intermediate Similarity	NPC476223
0.8444	Intermediate Similarity	NPC322159
0.8387	Intermediate Similarity	NPC472978
0.8387	Intermediate Similarity	NPC230064
0.8384	Intermediate Similarity	NPC118911
0.8372	Intermediate Similarity	NPC198240
0.837	Intermediate Similarity	NPC262043
0.837	Intermediate Similarity	NPC472973
0.837	Intermediate Similarity	NPC5509
0.8352	Intermediate Similarity	NPC136948
0.8333	Intermediate Similarity	NPC473456
0.8333	Intermediate Similarity	NPC474343
0.8333	Intermediate Similarity	NPC107243
0.8333	Intermediate Similarity	NPC65661
0.8333	Intermediate Similarity	NPC30984
0.8333	Intermediate Similarity	NPC476426
0.8333	Intermediate Similarity	NPC253826
0.8316	Intermediate Similarity	NPC134067
0.8315	Intermediate Similarity	NPC49019
0.8295	Intermediate Similarity	NPC229584
0.8295	Intermediate Similarity	NPC40228
0.8295	Intermediate Similarity	NPC90055
0.8295	Intermediate Similarity	NPC14203
0.8295	Intermediate Similarity	NPC327002
0.8283	Intermediate Similarity	NPC236390
0.828	Intermediate Similarity	NPC232202
0.828	Intermediate Similarity	NPC51486
0.828	Intermediate Similarity	NPC159748
0.828	Intermediate Similarity	NPC101651
0.828	Intermediate Similarity	NPC472866
0.8276	Intermediate Similarity	NPC476438
0.8276	Intermediate Similarity	NPC192999
0.8261	Intermediate Similarity	NPC104560
0.8261	Intermediate Similarity	NPC72397
0.8256	Intermediate Similarity	NPC165711
0.8256	Intermediate Similarity	NPC97377
0.8256	Intermediate Similarity	NPC61952
0.8247	Intermediate Similarity	NPC316598
0.8242	Intermediate Similarity	NPC472869
0.8211	Intermediate Similarity	NPC472977
0.8211	Intermediate Similarity	NPC472976
0.8202	Intermediate Similarity	NPC238991
0.8202	Intermediate Similarity	NPC302661
0.8191	Intermediate Similarity	NPC179517
0.8191	Intermediate Similarity	NPC474018
0.8191	Intermediate Similarity	NPC252433
0.8191	Intermediate Similarity	NPC165904
0.8191	Intermediate Similarity	NPC470113
0.8191	Intermediate Similarity	NPC472975
0.8191	Intermediate Similarity	NPC473986
0.8191	Intermediate Similarity	NPC476417
0.8182	Intermediate Similarity	NPC195290
0.8182	Intermediate Similarity	NPC204450
0.8172	Intermediate Similarity	NPC174342
0.8172	Intermediate Similarity	NPC36668
0.8172	Intermediate Similarity	NPC168131
0.8172	Intermediate Similarity	NPC469546
0.8172	Intermediate Similarity	NPC284561
0.8172	Intermediate Similarity	NPC281524
0.8172	Intermediate Similarity	NPC118011
0.8163	Intermediate Similarity	NPC287833
0.8163	Intermediate Similarity	NPC174314
0.8163	Intermediate Similarity	NPC51370
0.8163	Intermediate Similarity	NPC241221
0.8163	Intermediate Similarity	NPC471041
0.8161	Intermediate Similarity	NPC239098
0.8161	Intermediate Similarity	NPC62336
0.8161	Intermediate Similarity	NPC321514
0.8152	Intermediate Similarity	NPC231599
0.8144	Intermediate Similarity	NPC254496
0.8144	Intermediate Similarity	NPC475894
0.8144	Intermediate Similarity	NPC57416
0.8132	Intermediate Similarity	NPC474680
0.8132	Intermediate Similarity	NPC86316
0.8132	Intermediate Similarity	NPC106416
0.8132	Intermediate Similarity	NPC2709
0.8132	Intermediate Similarity	NPC189311
0.8125	Intermediate Similarity	NPC266899
0.8125	Intermediate Similarity	NPC274417
0.8125	Intermediate Similarity	NPC476174
0.8125	Intermediate Similarity	NPC53565
0.8125	Intermediate Similarity	NPC139459
0.8119	Intermediate Similarity	NPC472935
0.8119	Intermediate Similarity	NPC1679
0.8111	Intermediate Similarity	NPC476927
0.8111	Intermediate Similarity	NPC102197
0.8111	Intermediate Similarity	NPC97913
0.8105	Intermediate Similarity	NPC131840
0.8105	Intermediate Similarity	NPC169343
0.8105	Intermediate Similarity	NPC472871
0.8105	Intermediate Similarity	NPC474807
0.81	Intermediate Similarity	NPC90177
0.81	Intermediate Similarity	NPC95899
0.81	Intermediate Similarity	NPC95585
0.81	Intermediate Similarity	NPC282233
0.809	Intermediate Similarity	NPC471898
0.8085	Intermediate Similarity	NPC198818
0.8081	Intermediate Similarity	NPC99411
0.8081	Intermediate Similarity	NPC63249
0.8068	Intermediate Similarity	NPC327674
0.8065	Intermediate Similarity	NPC117122
0.8065	Intermediate Similarity	NPC471793
0.8065	Intermediate Similarity	NPC471791
0.8061	Intermediate Similarity	NPC197386
0.8061	Intermediate Similarity	NPC23364
0.8058	Intermediate Similarity	NPC137911
0.8058	Intermediate Similarity	NPC228477
0.8046	Intermediate Similarity	NPC472300
0.8043	Intermediate Similarity	NPC220478
0.8043	Intermediate Similarity	NPC324063
0.8043	Intermediate Similarity	NPC472974
0.8043	Intermediate Similarity	NPC73038
0.8041	Intermediate Similarity	NPC235053
0.8041	Intermediate Similarity	NPC29952
0.8041	Intermediate Similarity	NPC456
0.8041	Intermediate Similarity	NPC471463
0.8041	Intermediate Similarity	NPC29152
0.8041	Intermediate Similarity	NPC328371
0.8041	Intermediate Similarity	NPC472941
0.8039	Intermediate Similarity	NPC475294
0.8022	Intermediate Similarity	NPC248758
0.8022	Intermediate Similarity	NPC164577
0.8022	Intermediate Similarity	NPC472865
0.8022	Intermediate Similarity	NPC156981
0.8022	Intermediate Similarity	NPC19849
0.8022	Intermediate Similarity	NPC96095
0.8022	Intermediate Similarity	NPC472864
0.8021	Intermediate Similarity	NPC269729
0.8021	Intermediate Similarity	NPC159410
0.8021	Intermediate Similarity	NPC74751
0.8021	Intermediate Similarity	NPC184870
0.8021	Intermediate Similarity	NPC470958
0.8021	Intermediate Similarity	NPC470957
0.802	Intermediate Similarity	NPC472868
0.8	Intermediate Similarity	NPC477783
0.8	Intermediate Similarity	NPC56498
0.8	Intermediate Similarity	NPC15910
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC308726
0.8	Intermediate Similarity	NPC119601
0.8	Intermediate Similarity	NPC134077
0.8	Intermediate Similarity	NPC204341
0.8	Intermediate Similarity	NPC154101
0.8	Intermediate Similarity	NPC475320
0.8	Intermediate Similarity	NPC40918
0.8	Intermediate Similarity	NPC200513
0.8	Intermediate Similarity	NPC177037
0.8	Intermediate Similarity	NPC472814
0.7981	Intermediate Similarity	NPC37116
0.798	Intermediate Similarity	NPC205899
0.798	Intermediate Similarity	NPC471413
0.798	Intermediate Similarity	NPC218383
0.7979	Intermediate Similarity	NPC184663
0.7979	Intermediate Similarity	NPC474570
0.7979	Intermediate Similarity	NPC472983
0.7979	Intermediate Similarity	NPC123912
0.7979	Intermediate Similarity	NPC474700
0.7979	Intermediate Similarity	NPC66344
0.7978	Intermediate Similarity	NPC2482
0.7978	Intermediate Similarity	NPC104545
0.7978	Intermediate Similarity	NPC474956
0.7978	Intermediate Similarity	NPC37038
0.7961	Intermediate Similarity	NPC275539
0.7961	Intermediate Similarity	NPC189075
0.7959	Intermediate Similarity	NPC38530
0.7959	Intermediate Similarity	NPC285513
0.7959	Intermediate Similarity	NPC226986
0.7959	Intermediate Similarity	NPC121339
0.7959	Intermediate Similarity	NPC476253
0.7959	Intermediate Similarity	NPC84335
0.7959	Intermediate Similarity	NPC106557
0.7959	Intermediate Similarity	NPC156546
0.7957	Intermediate Similarity	NPC128644
0.7957	Intermediate Similarity	NPC477228
0.7957	Intermediate Similarity	NPC477926
0.7955	Intermediate Similarity	NPC275494
0.7955	Intermediate Similarity	NPC179028
0.7955	Intermediate Similarity	NPC471409
0.7955	Intermediate Similarity	NPC59436
0.7955	Intermediate Similarity	NPC74410

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 NPC476416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1405
0.2-0.3	3542
0.3-0.4	2550
0.4-0.5	962
0.5-0.6	245
0.6-0.7	154
0.7-0.8	118
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7902	Approved
0.8298	Intermediate Similarity	NPD6399	Phase 3
0.8021	Intermediate Similarity	NPD7748	Approved
0.8021	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD7900	Approved
0.8	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD6083	Phase 2
0.7905	Intermediate Similarity	NPD6650	Approved
0.7905	Intermediate Similarity	NPD6649	Approved
0.7885	Intermediate Similarity	NPD6372	Approved
0.7885	Intermediate Similarity	NPD6373	Approved
0.7879	Intermediate Similarity	NPD5696	Approved
0.7872	Intermediate Similarity	NPD6672	Approved
0.7872	Intermediate Similarity	NPD5737	Approved
0.7849	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD7146	Approved
0.7849	Intermediate Similarity	NPD7334	Approved
0.7849	Intermediate Similarity	NPD6409	Approved
0.7849	Intermediate Similarity	NPD5330	Approved
0.7849	Intermediate Similarity	NPD7521	Approved
0.7812	Intermediate Similarity	NPD7515	Phase 2
0.7788	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD4695	Discontinued
0.7767	Intermediate Similarity	NPD5739	Approved
0.7767	Intermediate Similarity	NPD6675	Approved
0.7767	Intermediate Similarity	NPD7128	Approved
0.7767	Intermediate Similarity	NPD6402	Approved
0.7766	Intermediate Similarity	NPD3573	Approved
0.7755	Intermediate Similarity	NPD5695	Phase 3
0.7692	Intermediate Similarity	NPD5697	Approved
0.7684	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6903	Approved
0.766	Intermediate Similarity	NPD4623	Approved
0.766	Intermediate Similarity	NPD4519	Discontinued
0.7642	Intermediate Similarity	NPD7290	Approved
0.7642	Intermediate Similarity	NPD6883	Approved
0.7642	Intermediate Similarity	NPD7102	Approved
0.7629	Intermediate Similarity	NPD5284	Approved
0.7629	Intermediate Similarity	NPD5281	Approved
0.7619	Intermediate Similarity	NPD7320	Approved
0.7619	Intermediate Similarity	NPD6011	Approved
0.7604	Intermediate Similarity	NPD6080	Approved
0.7604	Intermediate Similarity	NPD6904	Approved
0.7604	Intermediate Similarity	NPD6673	Approved
0.7576	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6847	Approved
0.757	Intermediate Similarity	NPD6617	Approved
0.757	Intermediate Similarity	NPD8130	Phase 1
0.757	Intermediate Similarity	NPD6869	Approved
0.7547	Intermediate Similarity	NPD6012	Approved
0.7547	Intermediate Similarity	NPD6013	Approved
0.7547	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7524	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7476	Intermediate Similarity	NPD5211	Phase 2
0.7474	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD3618	Phase 1
0.7453	Intermediate Similarity	NPD6686	Approved
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD5693	Phase 1
0.7449	Intermediate Similarity	NPD6079	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7423	Intermediate Similarity	NPD4753	Phase 2
0.7423	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5328	Approved
0.7419	Intermediate Similarity	NPD4223	Phase 3
0.7419	Intermediate Similarity	NPD4221	Approved
0.7407	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4629	Approved
0.74	Intermediate Similarity	NPD5210	Approved
0.7368	Intermediate Similarity	NPD1694	Approved
0.7368	Intermediate Similarity	NPD5329	Approved
0.7353	Intermediate Similarity	NPD7638	Approved
0.7353	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD5141	Approved
0.7327	Intermediate Similarity	NPD4697	Phase 3
0.7327	Intermediate Similarity	NPD7614	Phase 1
0.732	Intermediate Similarity	NPD5208	Approved
0.7292	Intermediate Similarity	NPD6098	Approved
0.7282	Intermediate Similarity	NPD4696	Approved
0.7282	Intermediate Similarity	NPD5285	Approved
0.7282	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD6050	Approved
0.7273	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7264	Intermediate Similarity	NPD6008	Approved
0.7263	Intermediate Similarity	NPD4786	Approved
0.7263	Intermediate Similarity	NPD4197	Approved
0.7255	Intermediate Similarity	NPD4755	Approved
0.7234	Intermediate Similarity	NPD3667	Approved
0.7212	Intermediate Similarity	NPD5223	Approved
0.72	Intermediate Similarity	NPD5779	Approved
0.72	Intermediate Similarity	NPD5778	Approved
0.72	Intermediate Similarity	NPD4202	Approved
0.7172	Intermediate Similarity	NPD5207	Approved
0.7172	Intermediate Similarity	NPD5692	Phase 3
0.7172	Intermediate Similarity	NPD5785	Approved
0.7168	Intermediate Similarity	NPD6335	Approved
0.7157	Intermediate Similarity	NPD5221	Approved
0.7157	Intermediate Similarity	NPD5222	Approved
0.7157	Intermediate Similarity	NPD7732	Phase 3
0.7157	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD4633	Approved
0.7143	Intermediate Similarity	NPD6274	Approved
0.7129	Intermediate Similarity	NPD6001	Approved
0.7117	Intermediate Similarity	NPD4632	Approved
0.7115	Intermediate Similarity	NPD4700	Approved
0.7113	Intermediate Similarity	NPD4689	Approved
0.7113	Intermediate Similarity	NPD4693	Phase 3
0.7113	Intermediate Similarity	NPD5205	Approved
0.7113	Intermediate Similarity	NPD4690	Approved
0.7113	Intermediate Similarity	NPD5279	Phase 3
0.7113	Intermediate Similarity	NPD4138	Approved
0.7113	Intermediate Similarity	NPD5690	Phase 2
0.7113	Intermediate Similarity	NPD4688	Approved
0.7105	Intermediate Similarity	NPD7100	Approved
0.7105	Intermediate Similarity	NPD7101	Approved
0.71	Intermediate Similarity	NPD5694	Approved
0.7087	Intermediate Similarity	NPD5173	Approved
0.708	Intermediate Similarity	NPD6317	Approved
0.7075	Intermediate Similarity	NPD5174	Approved
0.7075	Intermediate Similarity	NPD5175	Approved
0.7071	Intermediate Similarity	NPD6101	Approved
0.7071	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6412	Phase 2
0.7018	Intermediate Similarity	NPD6313	Approved
0.7018	Intermediate Similarity	NPD6314	Approved
0.701	Intermediate Similarity	NPD5363	Approved
0.6991	Remote Similarity	NPD6868	Approved
0.6989	Remote Similarity	NPD3617	Approved
0.6989	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4788	Approved
0.6952	Remote Similarity	NPD6404	Discontinued
0.6939	Remote Similarity	NPD4694	Approved
0.6939	Remote Similarity	NPD5280	Approved
0.6939	Remote Similarity	NPD5786	Approved
0.693	Remote Similarity	NPD6009	Approved
0.6916	Remote Similarity	NPD4754	Approved
0.6916	Remote Similarity	NPD6052	Approved
0.6915	Remote Similarity	NPD4195	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3668	Phase 3
0.69	Remote Similarity	NPD6051	Approved
0.6897	Remote Similarity	NPD7331	Phase 2
0.6897	Remote Similarity	NPD6319	Approved
0.6881	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6614	Approved
0.6875	Remote Similarity	NPD6053	Discontinued
0.6864	Remote Similarity	NPD7604	Phase 2
0.6848	Remote Similarity	NPD8039	Approved
0.6847	Remote Similarity	NPD6371	Approved
0.6838	Remote Similarity	NPD6908	Approved
0.6838	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD5983	Phase 2
0.6822	Remote Similarity	NPD7632	Discontinued
0.6818	Remote Similarity	NPD4730	Approved
0.6818	Remote Similarity	NPD5128	Approved
0.6818	Remote Similarity	NPD4729	Approved
0.6807	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD4768	Approved
0.6789	Remote Similarity	NPD4767	Approved
0.6782	Remote Similarity	NPD7341	Phase 2
0.6778	Remote Similarity	NPD4691	Approved
0.6765	Remote Similarity	NPD7637	Suspended
0.6757	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.675	Remote Similarity	NPD6336	Discontinued
0.6731	Remote Similarity	NPD5654	Approved
0.6723	Remote Similarity	NPD8328	Phase 3
0.6702	Remote Similarity	NPD4756	Discovery
0.6701	Remote Similarity	NPD6435	Approved
0.6701	Remote Similarity	NPD4269	Approved
0.6701	Remote Similarity	NPD4270	Approved
0.6698	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5251	Approved
0.6696	Remote Similarity	NPD5248	Approved
0.6696	Remote Similarity	NPD5249	Phase 3
0.6696	Remote Similarity	NPD4634	Approved
0.6696	Remote Similarity	NPD5247	Approved
0.6696	Remote Similarity	NPD5250	Approved
0.6696	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5135	Approved
0.6696	Remote Similarity	NPD5169	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)

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