NPASS Compound

Structure

NPC476409 OpenBabel07101719522D 25 27 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 -0.0000 -2.0000 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 1.0000 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 -2.5000 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 -0.0000 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 -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 0.3660 1.3660 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 2 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 -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 0.8660 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 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 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 1 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 1 0 0 0 19 20 1 1 0 0 0 20 5 1 6 0 0 0 21 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.23
Volume:	373.354
LogP:	3.053
LogD:	2.188
LogS:	-3.756
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	4.816
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.278
MDCK Permeability:	2.532320468162652e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.433
Plasma Protein Binding (PPB):	88.68782806396484%
Volume Distribution (VD):	0.427
Pgp-substrate:	12.984834671020508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.634
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.517
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.162
CYP3A4-substrate:	0.337

ADMET: Excretion

Clearance (CL):	1.61
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.623
Carcinogencity:	0.368
Eye Corrosion:	0.189
Eye Irritation:	0.905
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC476409

Natural Product ID:	NPC476409
*Common Name:**	13Beta-Hydroxy-7-Oxo-8(14)-Abieten-18-Oic Acid
IUPAC Name:	(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-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	KAYVLEFKNGBWRK-FZHKGVQDSA-N
Standard InCHI:	InChI=1S/C21H32O4/c1-13(2)21(25)10-7-15-14(11-21)16(22)12-20(5)18(15,3)8-6-9-19(20,4)17(23)24/h11,13,15,25H,6-10,12H2,1-5H3,(H,23,24)/t15-,18+,19-,20+,21+/m0/s1
SMILES:	CC(C)C1(CCC2C(=C1)C(=O)CC3(C2(CCCC3(C)C(=O)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL597746
PubChem CID:	46230315
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[537406]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[537406]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[537406]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[537406]

☑ 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 NPC476409 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	192
0.1-0.2	1170
0.2-0.3	4826
0.3-0.4	12088
0.4-0.5	11259
0.5-0.6	7221
0.6-0.7	4254
0.7-0.8	1523
0.8-0.85	123
0.85-0.9	28
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC476369
0.9412	High Similarity	NPC476437
0.9146	High Similarity	NPC302661
0.9146	High Similarity	NPC238991
0.9036	High Similarity	NPC102197
0.9024	High Similarity	NPC278459
0.8977	High Similarity	NPC131840
0.8977	High Similarity	NPC476416
0.8953	High Similarity	NPC48107
0.8929	High Similarity	NPC476412
0.8889	High Similarity	NPC198240
0.8851	High Similarity	NPC262043
0.8837	High Similarity	NPC136948
0.881	High Similarity	NPC49019
0.8765	High Similarity	NPC61952
0.8765	High Similarity	NPC165711
0.8765	High Similarity	NPC97377
0.8736	High Similarity	NPC72397
0.8721	High Similarity	NPC472869
0.8667	High Similarity	NPC476415
0.8652	High Similarity	NPC230064
0.8588	High Similarity	NPC97913
0.8571	High Similarity	NPC471898
0.8523	High Similarity	NPC117122
0.8523	High Similarity	NPC472870
0.8488	Intermediate Similarity	NPC96095
0.8488	Intermediate Similarity	NPC472864
0.8488	Intermediate Similarity	NPC164577
0.8488	Intermediate Similarity	NPC472865
0.8488	Intermediate Similarity	NPC248758
0.8488	Intermediate Similarity	NPC19849
0.8478	Intermediate Similarity	NPC472941
0.8478	Intermediate Similarity	NPC456
0.8452	Intermediate Similarity	NPC26139
0.8452	Intermediate Similarity	NPC37038
0.8444	Intermediate Similarity	NPC204341
0.8444	Intermediate Similarity	NPC472978
0.8434	Intermediate Similarity	NPC179028
0.8434	Intermediate Similarity	NPC471409
0.8434	Intermediate Similarity	NPC74410
0.8434	Intermediate Similarity	NPC275494
0.8427	Intermediate Similarity	NPC472973
0.8415	Intermediate Similarity	NPC180886
0.8404	Intermediate Similarity	NPC287833
0.8391	Intermediate Similarity	NPC29447
0.8391	Intermediate Similarity	NPC474537
0.8391	Intermediate Similarity	NPC8571
0.8387	Intermediate Similarity	NPC170131
0.8372	Intermediate Similarity	NPC105803
0.8353	Intermediate Similarity	NPC221647
0.8353	Intermediate Similarity	NPC40228
0.8353	Intermediate Similarity	NPC90055
0.8333	Intermediate Similarity	NPC231431
0.8333	Intermediate Similarity	NPC472866
0.8333	Intermediate Similarity	NPC170394
0.8315	Intermediate Similarity	NPC104560
0.8295	Intermediate Similarity	NPC186975
0.8295	Intermediate Similarity	NPC322159
0.8293	Intermediate Similarity	NPC476795
0.8261	Intermediate Similarity	NPC472976
0.8261	Intermediate Similarity	NPC472977
0.8256	Intermediate Similarity	NPC472867
0.8256	Intermediate Similarity	NPC472239
0.8256	Intermediate Similarity	NPC320514
0.8242	Intermediate Similarity	NPC474018
0.8242	Intermediate Similarity	NPC473986
0.8235	Intermediate Similarity	NPC476809
0.8222	Intermediate Similarity	NPC36668
0.8222	Intermediate Similarity	NPC469546
0.8222	Intermediate Similarity	NPC281524
0.8222	Intermediate Similarity	NPC118011
0.8222	Intermediate Similarity	NPC184663
0.8222	Intermediate Similarity	NPC477973
0.8214	Intermediate Similarity	NPC280654
0.8214	Intermediate Similarity	NPC260385
0.8214	Intermediate Similarity	NPC110094
0.8214	Intermediate Similarity	NPC239098
0.8214	Intermediate Similarity	NPC62336
0.8214	Intermediate Similarity	NPC321514
0.8211	Intermediate Similarity	NPC51370
0.8202	Intermediate Similarity	NPC236618
0.8191	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC94531
0.8182	Intermediate Similarity	NPC476426
0.8182	Intermediate Similarity	NPC123319
0.8182	Intermediate Similarity	NPC474680
0.8182	Intermediate Similarity	NPC142649
0.8182	Intermediate Similarity	NPC311702
0.8182	Intermediate Similarity	NPC473038
0.8182	Intermediate Similarity	NPC269638
0.8172	Intermediate Similarity	NPC476174
0.8171	Intermediate Similarity	NPC103958
0.8171	Intermediate Similarity	NPC18819
0.8171	Intermediate Similarity	NPC161923
0.8171	Intermediate Similarity	NPC183503
0.8171	Intermediate Similarity	NPC283908
0.8171	Intermediate Similarity	NPC46610
0.8152	Intermediate Similarity	NPC472871
0.8152	Intermediate Similarity	NPC151722
0.8148	Intermediate Similarity	NPC133253
0.8148	Intermediate Similarity	NPC21944
0.814	Intermediate Similarity	NPC189237
0.814	Intermediate Similarity	NPC162632
0.814	Intermediate Similarity	NPC473217
0.814	Intermediate Similarity	NPC142244
0.814	Intermediate Similarity	NPC274050
0.814	Intermediate Similarity	NPC477372
0.814	Intermediate Similarity	NPC147066
0.814	Intermediate Similarity	NPC263272
0.814	Intermediate Similarity	NPC267691
0.8125	Intermediate Similarity	NPC115862
0.8118	Intermediate Similarity	NPC192329
0.8118	Intermediate Similarity	NPC199595
0.8105	Intermediate Similarity	NPC478056
0.8105	Intermediate Similarity	NPC197386
0.8095	Intermediate Similarity	NPC472300
0.8095	Intermediate Similarity	NPC257666
0.8095	Intermediate Similarity	NPC107039
0.8095	Intermediate Similarity	NPC471899
0.8095	Intermediate Similarity	NPC471897
0.8095	Intermediate Similarity	NPC132542
0.8095	Intermediate Similarity	NPC266193
0.809	Intermediate Similarity	NPC472974
0.8085	Intermediate Similarity	NPC29152
0.8072	Intermediate Similarity	NPC279666
0.8072	Intermediate Similarity	NPC192540
0.8072	Intermediate Similarity	NPC476346
0.8068	Intermediate Similarity	NPC156981
0.8065	Intermediate Similarity	NPC470957
0.8065	Intermediate Similarity	NPC470958
0.8049	Intermediate Similarity	NPC35656
0.8049	Intermediate Similarity	NPC247586
0.8049	Intermediate Similarity	NPC56747
0.8049	Intermediate Similarity	NPC180015
0.8049	Intermediate Similarity	NPC130016
0.8049	Intermediate Similarity	NPC109576
0.8046	Intermediate Similarity	NPC251779
0.8046	Intermediate Similarity	NPC142253
0.8046	Intermediate Similarity	NPC3511
0.8046	Intermediate Similarity	NPC69101
0.8043	Intermediate Similarity	NPC472975
0.8041	Intermediate Similarity	NPC293753
0.8023	Intermediate Similarity	NPC104545
0.8023	Intermediate Similarity	NPC2482
0.8022	Intermediate Similarity	NPC5509
0.8022	Intermediate Similarity	NPC66344
0.8	Intermediate Similarity	NPC476253
0.8	Intermediate Similarity	NPC477228
0.8	Intermediate Similarity	NPC59436
0.8	Intermediate Similarity	NPC231599
0.8	Intermediate Similarity	NPC471792
0.8	Intermediate Similarity	NPC128644
0.8	Intermediate Similarity	NPC156546
0.8	Intermediate Similarity	NPC473456
0.798	Intermediate Similarity	NPC472935
0.7979	Intermediate Similarity	NPC174948
0.7979	Intermediate Similarity	NPC37646
0.7979	Intermediate Similarity	NPC173875
0.7979	Intermediate Similarity	NPC147232
0.7979	Intermediate Similarity	NPC266899
0.7979	Intermediate Similarity	NPC318282
0.7979	Intermediate Similarity	NPC469995
0.7979	Intermediate Similarity	NPC171395
0.7978	Intermediate Similarity	NPC65661
0.7978	Intermediate Similarity	NPC11711
0.7978	Intermediate Similarity	NPC60350
0.7976	Intermediate Similarity	NPC263582
0.7976	Intermediate Similarity	NPC69143
0.7976	Intermediate Similarity	NPC472305
0.7976	Intermediate Similarity	NPC89294
0.7959	Intermediate Similarity	NPC478057
0.7955	Intermediate Similarity	NPC297398
0.7955	Intermediate Similarity	NPC70834
0.7955	Intermediate Similarity	NPC279639
0.7955	Intermediate Similarity	NPC470015
0.7955	Intermediate Similarity	NPC168188
0.7955	Intermediate Similarity	NPC3856
0.7955	Intermediate Similarity	NPC477373
0.7952	Intermediate Similarity	NPC251970
0.7952	Intermediate Similarity	NPC476046
0.7952	Intermediate Similarity	NPC241854
0.7938	Intermediate Similarity	NPC472924
0.7935	Intermediate Similarity	NPC51486
0.7935	Intermediate Similarity	NPC198818
0.7931	Intermediate Similarity	NPC229584
0.7931	Intermediate Similarity	NPC44963
0.7931	Intermediate Similarity	NPC226068
0.7931	Intermediate Similarity	NPC472684
0.7931	Intermediate Similarity	NPC201912
0.7931	Intermediate Similarity	NPC327002
0.7931	Intermediate Similarity	NPC55869
0.7931	Intermediate Similarity	NPC38350
0.7931	Intermediate Similarity	NPC14203
0.7927	Intermediate Similarity	NPC160817
0.7917	Intermediate Similarity	NPC471717
0.7917	Intermediate Similarity	NPC166745
0.7917	Intermediate Similarity	NPC235464
0.7912	Intermediate Similarity	NPC124927
0.7912	Intermediate Similarity	NPC475101
0.7912	Intermediate Similarity	NPC476427

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 NPC476409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1536
0.2-0.3	3732
0.3-0.4	2443
0.4-0.5	774
0.5-0.6	243
0.6-0.7	150
0.7-0.8	88
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
0.8235	Intermediate Similarity	NPD4695	Discontinued
0.809	Intermediate Similarity	NPD4519	Discontinued
0.809	Intermediate Similarity	NPD4623	Approved
0.8085	Intermediate Similarity	NPD7614	Phase 1
0.7849	Intermediate Similarity	NPD7515	Phase 2
0.7841	Intermediate Similarity	NPD4221	Approved
0.7841	Intermediate Similarity	NPD4223	Phase 3
0.7826	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD3573	Approved
0.7778	Intermediate Similarity	NPD5329	Approved
0.7732	Intermediate Similarity	NPD5696	Approved
0.7692	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7748	Approved
0.7667	Intermediate Similarity	NPD4197	Approved
0.766	Intermediate Similarity	NPD5281	Approved
0.766	Intermediate Similarity	NPD5284	Approved
0.764	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6673	Approved
0.7634	Intermediate Similarity	NPD6904	Approved
0.7634	Intermediate Similarity	NPD6080	Approved
0.7629	Intermediate Similarity	NPD6084	Phase 2
0.7629	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD4629	Approved
0.7604	Intermediate Similarity	NPD5210	Approved
0.7527	Intermediate Similarity	NPD6672	Approved
0.7527	Intermediate Similarity	NPD5737	Approved
0.7526	Intermediate Similarity	NPD7732	Phase 3
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7474	Intermediate Similarity	NPD5693	Phase 1
0.7474	Intermediate Similarity	NPD6079	Approved
0.7473	Intermediate Similarity	NPD3666	Approved
0.7473	Intermediate Similarity	NPD3665	Phase 1
0.7473	Intermediate Similarity	NPD3133	Approved
0.7449	Intermediate Similarity	NPD7902	Approved
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD4753	Phase 2
0.7423	Intermediate Similarity	NPD5695	Phase 3
0.7396	Intermediate Similarity	NPD6399	Phase 3
0.7386	Intermediate Similarity	NPD3617	Approved
0.734	Intermediate Similarity	NPD5208	Approved
0.734	Intermediate Similarity	NPD6903	Approved
0.734	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5211	Phase 2
0.7317	Intermediate Similarity	NPD7331	Phase 2
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7312	Intermediate Similarity	NPD5280	Approved
0.7312	Intermediate Similarity	NPD4694	Approved
0.7312	Intermediate Similarity	NPD6098	Approved
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7303	Intermediate Similarity	NPD4195	Approved
0.73	Intermediate Similarity	NPD6404	Discontinued
0.7292	Intermediate Similarity	NPD6050	Approved
0.7283	Intermediate Similarity	NPD4786	Approved
0.7282	Intermediate Similarity	NPD5739	Approved
0.7282	Intermediate Similarity	NPD6675	Approved
0.7282	Intermediate Similarity	NPD6402	Approved
0.7282	Intermediate Similarity	NPD7128	Approved
0.7253	Intermediate Similarity	NPD3667	Approved
0.7245	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5697	Approved
0.7195	Intermediate Similarity	NPD7341	Phase 2
0.7188	Intermediate Similarity	NPD5692	Phase 3
0.7184	Intermediate Similarity	NPD5141	Approved
0.7176	Intermediate Similarity	NPD4691	Approved
0.7172	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5221	Approved
0.7172	Intermediate Similarity	NPD5222	Approved
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7157	Intermediate Similarity	NPD5091	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD7640	Approved
0.7129	Intermediate Similarity	NPD7639	Approved
0.7129	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7113	Intermediate Similarity	NPD5694	Approved
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.71	Intermediate Similarity	NPD5173	Approved
0.71	Intermediate Similarity	NPD4755	Approved
0.7091	Intermediate Similarity	NPD7115	Discovery
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7075	Intermediate Similarity	NPD6373	Approved
0.7075	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD4137	Phase 3
0.7048	Intermediate Similarity	NPD5701	Approved
0.7048	Intermediate Similarity	NPD6614	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.7037	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD8297	Approved
0.703	Intermediate Similarity	NPD7638	Approved
0.701	Intermediate Similarity	NPD4096	Approved
0.701	Intermediate Similarity	NPD5207	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4697	Phase 3
0.699	Remote Similarity	NPD5226	Approved
0.699	Remote Similarity	NPD5225	Approved
0.699	Remote Similarity	NPD4633	Approved
0.699	Remote Similarity	NPD5224	Approved
0.6989	Remote Similarity	NPD4788	Approved
0.6981	Remote Similarity	NPD6686	Approved
0.6977	Remote Similarity	NPD4747	Approved
0.697	Remote Similarity	NPD6001	Approved
0.6961	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6411	Approved
0.6932	Remote Similarity	NPD4058	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6915	Remote Similarity	NPD3668	Phase 3
0.6897	Remote Similarity	NPD6081	Approved
0.6869	Remote Similarity	NPD5779	Approved
0.6869	Remote Similarity	NPD5778	Approved
0.6863	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD1694	Approved
0.6842	Remote Similarity	NPD5363	Approved
0.6837	Remote Similarity	NPD5785	Approved
0.6818	Remote Similarity	NPD4632	Approved
0.6804	Remote Similarity	NPD4518	Approved
0.6774	Remote Similarity	NPD4139	Approved
0.6774	Remote Similarity	NPD4692	Approved
0.6762	Remote Similarity	NPD6052	Approved
0.6762	Remote Similarity	NPD4754	Approved
0.6742	Remote Similarity	NPD5733	Approved
0.6735	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6101	Approved
0.6733	Remote Similarity	NPD5654	Approved
0.6726	Remote Similarity	NPD6335	Approved
0.6705	Remote Similarity	NPD5276	Approved
0.6705	Remote Similarity	NPD4243	Approved
0.6703	Remote Similarity	NPD4756	Discovery
0.67	Remote Similarity	NPD5133	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6696	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD7101	Approved
0.6637	Remote Similarity	NPD6317	Approved
0.6637	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD4767	Approved
0.6602	Remote Similarity	NPD5959	Approved
0.6579	Remote Similarity	NPD6314	Approved
0.6579	Remote Similarity	NPD6313	Approved
0.6574	Remote Similarity	NPD6412	Phase 2
0.6566	Remote Similarity	NPD6051	Approved
0.6556	Remote Similarity	NPD4687	Approved
0.6556	Remote Similarity	NPD4784	Approved
0.6556	Remote Similarity	NPD4785	Approved
0.6552	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5135	Approved
0.6545	Remote Similarity	NPD5169	Approved
0.6545	Remote Similarity	NPD5250	Approved
0.6545	Remote Similarity	NPD5251	Approved
0.6545	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5247	Approved
0.6545	Remote Similarity	NPD4634	Approved
0.6545	Remote Similarity	NPD5249	Phase 3
0.6545	Remote Similarity	NPD5248	Approved
0.6526	Remote Similarity	NPD4269	Approved
0.6526	Remote Similarity	NPD4270	Approved
0.6514	Remote Similarity	NPD5168	Approved
0.6512	Remote Similarity	NPD4224	Phase 2
0.6509	Remote Similarity	NPD7632	Discontinued
0.6486	Remote Similarity	NPD5216	Approved
0.6486	Remote Similarity	NPD5127	Approved
0.6486	Remote Similarity	NPD5217	Approved
0.6486	Remote Similarity	NPD5215	Approved
0.6484	Remote Similarity	NPD8039	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