NPASS Compound

Structure

NPC165904 OpenBabel07101718292D 25 27 0 0 1 0 0 0 0 0999 V2000 2.5075 1.2831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5802 0.3918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9716 0.2831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3829 2.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1056 -2.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9716 -1.7169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2396 -1.7169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2396 1.2831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1488 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1056 0.7831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1147 -1.1829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5981 0.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4540 -0.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3735 0.7831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4417 -0.7346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9716 -0.7169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2396 -0.7169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8376 -0.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3735 -0.2169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1056 -0.2169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7037 -0.7169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8376 0.7831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5507 1.6948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 10 21 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 20 1 6 0 0 0 15 9 1 6 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 17 21 1 0 0 0 0 18 24 1 6 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.25
Volume:	375.991
LogP:	3.874
LogD:	3.023
LogS:	-4.306
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	4.629
Fsp3:	0.857
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:	-4.921
MDCK Permeability:	2.822667738655582e-05
Pgp-inhibitor:	0.421
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	96.3862075805664%
Volume Distribution (VD):	0.585
Pgp-substrate:	3.6465988159179688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.752
CYP2C9-inhibitor:	0.141
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	2.827
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.964
Carcinogencity:	0.113
Eye Corrosion:	0.571
Eye Irritation:	0.92
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC165904

Natural Product ID:	NPC165904
*Common Name:**	13-Epi-15,16-Epoxy-15Alphamethoxy-Ent-Clerod-3-En-18-Oic Acid
IUPAC Name:	(4aR,5S,6R,8aR)-5-[2-[(3S,5S)-5-methoxyoxolan-3-yl]ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	AGZLUBWOHWIZBV-UNJZARNNSA-N
Standard InCHI:	InChI=1S/C21H34O4/c1-14-8-10-21(3)16(19(22)23)6-5-7-17(21)20(14,2)11-9-15-12-18(24-4)25-13-15/h6,14-15,17-18H,5,7-13H2,1-4H3,(H,22,23)/t14-,15+,17-,18+,20+,21+/m1/s1
SMILES:	CO[C@H]1OC[C@H](C1)CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CCC=C2C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520592
PubChem CID:	11566481
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
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16499330]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7931367]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	53.0	%	PMID[486821]

☑ 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 NPC165904 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	164
0.1-0.2	1059
0.2-0.3	4951
0.3-0.4	12538
0.4-0.5	9884
0.5-0.6	6358
0.6-0.7	6317
0.7-0.8	1364
0.8-0.85	55
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179517
0.8889	High Similarity	NPC65513
0.8842	High Similarity	NPC134077
0.8791	High Similarity	NPC166346
0.8737	High Similarity	NPC63249
0.8681	High Similarity	NPC477783
0.8617	High Similarity	NPC204054
0.8617	High Similarity	NPC257726
0.8571	High Similarity	NPC477782
0.8539	High Similarity	NPC474062
0.8523	High Similarity	NPC71626
0.8495	Intermediate Similarity	NPC474554
0.8462	Intermediate Similarity	NPC251528
0.8409	Intermediate Similarity	NPC97913
0.8387	Intermediate Similarity	NPC267266
0.8387	Intermediate Similarity	NPC277721
0.8316	Intermediate Similarity	NPC17578
0.8316	Intermediate Similarity	NPC240673
0.8315	Intermediate Similarity	NPC164577
0.8315	Intermediate Similarity	NPC472865
0.828	Intermediate Similarity	NPC470113
0.828	Intermediate Similarity	NPC141831
0.8261	Intermediate Similarity	NPC168131
0.8261	Intermediate Similarity	NPC5509
0.8261	Intermediate Similarity	NPC174342
0.8247	Intermediate Similarity	NPC477720
0.8229	Intermediate Similarity	NPC475709
0.8222	Intermediate Similarity	NPC473251
0.8222	Intermediate Similarity	NPC65661
0.8222	Intermediate Similarity	NPC42586
0.8202	Intermediate Similarity	NPC472440
0.8191	Intermediate Similarity	NPC151722
0.8191	Intermediate Similarity	NPC470656
0.8191	Intermediate Similarity	NPC476416
0.8172	Intermediate Similarity	NPC232426
0.8172	Intermediate Similarity	NPC469403
0.8172	Intermediate Similarity	NPC281942
0.8161	Intermediate Similarity	NPC327674
0.8152	Intermediate Similarity	NPC472870
0.8144	Intermediate Similarity	NPC473154
0.8132	Intermediate Similarity	NPC244174
0.8125	Intermediate Similarity	NPC325960
0.8125	Intermediate Similarity	NPC470801
0.8125	Intermediate Similarity	NPC319692
0.8125	Intermediate Similarity	NPC112654
0.8111	Intermediate Similarity	NPC19849
0.8111	Intermediate Similarity	NPC472864
0.8105	Intermediate Similarity	NPC474555
0.8085	Intermediate Similarity	NPC252433
0.8085	Intermediate Similarity	NPC477122
0.8065	Intermediate Similarity	NPC470734
0.8065	Intermediate Similarity	NPC66344
0.8061	Intermediate Similarity	NPC476274
0.8058	Intermediate Similarity	NPC235014
0.8046	Intermediate Similarity	NPC198240
0.8041	Intermediate Similarity	NPC476253
0.8022	Intermediate Similarity	NPC106416
0.8022	Intermediate Similarity	NPC300985
0.8022	Intermediate Similarity	NPC189311
0.8022	Intermediate Similarity	NPC472442
0.8022	Intermediate Similarity	NPC86316
0.8021	Intermediate Similarity	NPC473369
0.8021	Intermediate Similarity	NPC293052
0.802	Intermediate Similarity	NPC127790
0.8	Intermediate Similarity	NPC115021
0.8	Intermediate Similarity	NPC157441
0.8	Intermediate Similarity	NPC472303
0.8	Intermediate Similarity	NPC471364
0.8	Intermediate Similarity	NPC471365
0.8	Intermediate Similarity	NPC132395
0.8	Intermediate Similarity	NPC22611
0.798	Intermediate Similarity	NPC476223
0.798	Intermediate Similarity	NPC224720
0.798	Intermediate Similarity	NPC476240
0.798	Intermediate Similarity	NPC471075
0.7979	Intermediate Similarity	NPC472866
0.7978	Intermediate Similarity	NPC229584
0.7978	Intermediate Similarity	NPC40228
0.7978	Intermediate Similarity	NPC327002
0.7978	Intermediate Similarity	NPC14203
0.7957	Intermediate Similarity	NPC226863
0.7938	Intermediate Similarity	NPC311166
0.7935	Intermediate Similarity	NPC186975
0.7935	Intermediate Similarity	NPC472869
0.7931	Intermediate Similarity	NPC61952
0.7917	Intermediate Similarity	NPC475572
0.7917	Intermediate Similarity	NPC476415
0.7917	Intermediate Similarity	NPC298973
0.7917	Intermediate Similarity	NPC104925
0.7912	Intermediate Similarity	NPC248758
0.7907	Intermediate Similarity	NPC476795
0.7905	Intermediate Similarity	NPC12046
0.7905	Intermediate Similarity	NPC194951
0.7895	Intermediate Similarity	NPC289479
0.7895	Intermediate Similarity	NPC474018
0.7895	Intermediate Similarity	NPC473986
0.7895	Intermediate Similarity	NPC476187
0.7889	Intermediate Similarity	NPC200513
0.7879	Intermediate Similarity	NPC241221
0.7865	Intermediate Similarity	NPC473685
0.7864	Intermediate Similarity	NPC469844
0.7864	Intermediate Similarity	NPC392
0.7864	Intermediate Similarity	NPC177524
0.7864	Intermediate Similarity	NPC219900
0.7857	Intermediate Similarity	NPC76266
0.7857	Intermediate Similarity	NPC98112
0.7857	Intermediate Similarity	NPC170131
0.7849	Intermediate Similarity	NPC167877
0.7849	Intermediate Similarity	NPC475678
0.7849	Intermediate Similarity	NPC236618
0.7849	Intermediate Similarity	NPC312561
0.7843	Intermediate Similarity	NPC252296
0.7841	Intermediate Similarity	NPC239098
0.7841	Intermediate Similarity	NPC321514
0.7835	Intermediate Similarity	NPC183012
0.7826	Intermediate Similarity	NPC474860
0.7826	Intermediate Similarity	NPC52628
0.7826	Intermediate Similarity	NPC30984
0.7826	Intermediate Similarity	NPC217394
0.7826	Intermediate Similarity	NPC471300
0.7812	Intermediate Similarity	NPC472871
0.7812	Intermediate Similarity	NPC242069
0.7812	Intermediate Similarity	NPC471571
0.7812	Intermediate Similarity	NPC469939
0.7802	Intermediate Similarity	NPC469
0.7802	Intermediate Similarity	NPC49019
0.78	Intermediate Similarity	NPC472643
0.78	Intermediate Similarity	NPC99411
0.7798	Intermediate Similarity	NPC474179
0.7798	Intermediate Similarity	NPC475834
0.7789	Intermediate Similarity	NPC51486
0.7789	Intermediate Similarity	NPC477149
0.7789	Intermediate Similarity	NPC477147
0.7788	Intermediate Similarity	NPC112457
0.7778	Intermediate Similarity	NPC478056
0.7778	Intermediate Similarity	NPC149237
0.7778	Intermediate Similarity	NPC23364
0.7778	Intermediate Similarity	NPC23046
0.7778	Intermediate Similarity	NPC278459
0.7767	Intermediate Similarity	NPC184512
0.7766	Intermediate Similarity	NPC104560
0.7766	Intermediate Similarity	NPC117122
0.7766	Intermediate Similarity	NPC472810
0.7766	Intermediate Similarity	NPC472809
0.7755	Intermediate Similarity	NPC472941
0.7755	Intermediate Similarity	NPC456
0.7745	Intermediate Similarity	NPC146731
0.7742	Intermediate Similarity	NPC322159
0.7742	Intermediate Similarity	NPC473226
0.7742	Intermediate Similarity	NPC118266
0.7732	Intermediate Similarity	NPC477130
0.7732	Intermediate Similarity	NPC324078
0.7732	Intermediate Similarity	NPC184870
0.7732	Intermediate Similarity	NPC469697
0.7732	Intermediate Similarity	NPC477129
0.7732	Intermediate Similarity	NPC88507
0.7727	Intermediate Similarity	NPC97377
0.7727	Intermediate Similarity	NPC316500
0.7723	Intermediate Similarity	NPC471363
0.7723	Intermediate Similarity	NPC476769
0.7723	Intermediate Similarity	NPC58329
0.7723	Intermediate Similarity	NPC238397
0.7723	Intermediate Similarity	NPC136289
0.7717	Intermediate Similarity	NPC165064
0.7708	Intermediate Similarity	NPC177037
0.7708	Intermediate Similarity	NPC472814
0.7708	Intermediate Similarity	NPC474631
0.7708	Intermediate Similarity	NPC186363
0.7708	Intermediate Similarity	NPC233345
0.7706	Intermediate Similarity	NPC475913
0.77	Intermediate Similarity	NPC476767
0.77	Intermediate Similarity	NPC472644
0.77	Intermediate Similarity	NPC471041
0.7692	Intermediate Similarity	NPC325054
0.7692	Intermediate Similarity	NPC256112
0.7692	Intermediate Similarity	NPC300614
0.7692	Intermediate Similarity	NPC122945
0.7692	Intermediate Similarity	NPC186276
0.7692	Intermediate Similarity	NPC90946
0.7692	Intermediate Similarity	NPC470024
0.7692	Intermediate Similarity	NPC109938
0.7684	Intermediate Similarity	NPC118011
0.7684	Intermediate Similarity	NPC293044
0.7684	Intermediate Similarity	NPC472983
0.7684	Intermediate Similarity	NPC262043
0.7684	Intermediate Similarity	NPC214387
0.7684	Intermediate Similarity	NPC284561
0.7684	Intermediate Similarity	NPC36668
0.7677	Intermediate Similarity	NPC208094
0.7677	Intermediate Similarity	NPC475894
0.7677	Intermediate Similarity	NPC253826
0.7677	Intermediate Similarity	NPC474343
0.7674	Intermediate Similarity	NPC35656
0.767	Intermediate Similarity	NPC218158
0.767	Intermediate Similarity	NPC172867
0.7667	Intermediate Similarity	NPC271104
0.7667	Intermediate Similarity	NPC477057
0.7667	Intermediate Similarity	NPC195424
0.7667	Intermediate Similarity	NPC104545
0.7664	Intermediate Similarity	NPC293658

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 NPC165904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1482
0.2-0.3	3900
0.3-0.4	2440
0.4-0.5	702
0.5-0.6	229
0.6-0.7	215
0.7-0.8	42
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
0.7889	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD6686	Approved
0.7449	Intermediate Similarity	NPD6399	Phase 3
0.7447	Intermediate Similarity	NPD1694	Approved
0.7429	Intermediate Similarity	NPD6412	Phase 2
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7374	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD6083	Phase 2
0.7327	Intermediate Similarity	NPD7902	Approved
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7248	Intermediate Similarity	NPD6882	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7640	Approved
0.7184	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7515	Phase 2
0.7158	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4225	Approved
0.7087	Intermediate Similarity	NPD7638	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7037	Intermediate Similarity	NPD6899	Approved
0.7037	Intermediate Similarity	NPD6881	Approved
0.703	Intermediate Similarity	NPD7900	Approved
0.703	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6404	Discontinued
0.701	Intermediate Similarity	NPD4519	Discontinued
0.701	Intermediate Similarity	NPD4623	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.6979	Remote Similarity	NPD3666	Approved
0.6979	Remote Similarity	NPD3133	Approved
0.6979	Remote Similarity	NPD3665	Phase 1
0.697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD6904	Approved
0.697	Remote Similarity	NPD6080	Approved
0.6961	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5697	Approved
0.6915	Remote Similarity	NPD4695	Discontinued
0.6909	Remote Similarity	NPD7290	Approved
0.6909	Remote Similarity	NPD7102	Approved
0.6909	Remote Similarity	NPD6883	Approved
0.6881	Remote Similarity	NPD6011	Approved
0.6881	Remote Similarity	NPD7320	Approved
0.6847	Remote Similarity	NPD6650	Approved
0.6847	Remote Similarity	NPD6869	Approved
0.6847	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD8130	Phase 1
0.6847	Remote Similarity	NPD6617	Approved
0.6842	Remote Similarity	NPD7115	Discovery
0.6838	Remote Similarity	NPD6370	Approved
0.6837	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3618	Phase 1
0.6833	Remote Similarity	NPD7736	Approved
0.6832	Remote Similarity	NPD5693	Phase 1
0.6832	Remote Similarity	NPD6050	Approved
0.6832	Remote Similarity	NPD6079	Approved
0.6818	Remote Similarity	NPD6013	Approved
0.6818	Remote Similarity	NPD6014	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.6818	Remote Similarity	NPD6012	Approved
0.6818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6373	Approved
0.6807	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD4786	Approved
0.68	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD4753	Phase 2
0.6789	Remote Similarity	NPD5701	Approved
0.6786	Remote Similarity	NPD8297	Approved
0.6771	Remote Similarity	NPD3667	Approved
0.6771	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4221	Approved
0.6768	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.675	Remote Similarity	NPD8293	Discontinued
0.6739	Remote Similarity	NPD8039	Approved
0.6735	Remote Similarity	NPD5329	Approved
0.6733	Remote Similarity	NPD5785	Approved
0.6733	Remote Similarity	NPD5692	Phase 3
0.6733	Remote Similarity	NPD5207	Approved
0.6731	Remote Similarity	NPD7614	Phase 1
0.6729	Remote Similarity	NPD7632	Discontinued
0.6729	Remote Similarity	NPD5211	Phase 2
0.6723	Remote Similarity	NPD7492	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5208	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD6067	Discontinued
0.6635	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4629	Approved
0.6635	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD4197	Approved
0.6612	Remote Similarity	NPD7078	Approved
0.661	Remote Similarity	NPD7503	Approved
0.6607	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5141	Approved
0.6602	Remote Similarity	NPD4202	Approved
0.6571	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5222	Approved
0.6571	Remote Similarity	NPD7732	Phase 3
0.6571	Remote Similarity	NPD5221	Approved
0.6566	Remote Similarity	NPD5363	Approved
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4696	Approved
0.6542	Remote Similarity	NPD5286	Approved
0.6542	Remote Similarity	NPD5285	Approved
0.6538	Remote Similarity	NPD6001	Approved
0.6531	Remote Similarity	NPD7154	Phase 3
0.6531	Remote Similarity	NPD5362	Discontinued
0.6525	Remote Similarity	NPD6059	Approved
0.6509	Remote Similarity	NPD5173	Approved
0.6509	Remote Similarity	NPD4755	Approved
0.6505	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD5280	Approved
0.65	Remote Similarity	NPD4694	Approved
0.65	Remote Similarity	NPD4693	Phase 3
0.65	Remote Similarity	NPD5205	Approved
0.65	Remote Similarity	NPD4688	Approved
0.65	Remote Similarity	NPD4138	Approved
0.65	Remote Similarity	NPD4690	Approved
0.6496	Remote Similarity	NPD6335	Approved
0.6496	Remote Similarity	NPD7327	Approved
0.6496	Remote Similarity	NPD7328	Approved
0.6491	Remote Similarity	NPD6053	Discontinued
0.6481	Remote Similarity	NPD5223	Approved
0.6476	Remote Similarity	NPD5654	Approved
0.6471	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6051	Approved
0.6466	Remote Similarity	NPD6274	Approved
0.6466	Remote Similarity	NPD6868	Approved
0.6465	Remote Similarity	NPD3668	Phase 3
0.6452	Remote Similarity	NPD6914	Discontinued
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7101	Approved
0.6441	Remote Similarity	NPD7516	Approved
0.6441	Remote Similarity	NPD7100	Approved
0.6435	Remote Similarity	NPD4632	Approved
0.6435	Remote Similarity	NPD8133	Approved
0.6422	Remote Similarity	NPD5226	Approved
0.6422	Remote Similarity	NPD5224	Approved
0.6422	Remote Similarity	NPD5225	Approved
0.6422	Remote Similarity	NPD4633	Approved
0.6417	Remote Similarity	NPD5988	Approved
0.6415	Remote Similarity	NPD4697	Phase 3
0.641	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6317	Approved
0.6408	Remote Similarity	NPD6698	Approved
0.6408	Remote Similarity	NPD46	Approved
0.64	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1696	Phase 3
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4700	Approved
0.6387	Remote Similarity	NPD8294	Approved
0.6387	Remote Similarity	NPD8377	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD4788	Approved
0.6364	Remote Similarity	NPD7122	Discontinued
0.6364	Remote Similarity	NPD6052	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD6313	Approved
0.6356	Remote Similarity	NPD6314	Approved
0.6355	Remote Similarity	NPD5959	Approved
0.6339	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8296	Approved
0.6333	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8515	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