NPASS Compound

Structure

NPC242957 OpenBabel07101719152D 28 32 0 0 1 0 0 0 0 0999 V2000 7.9509 -0.8272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6921 -1.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2438 -0.1201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7262 -2.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2779 -0.3789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8771 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0191 -1.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 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 -1.1249 1.6238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3611 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0580 3.1533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3482 2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3173 4.0802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7036 3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9801 1.8040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 2 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 15 1 0 0 0 0 11 12 2 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 16 10 1 6 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 11 1 1 0 0 0 17 23 1 0 0 0 0 18 12 1 1 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 13 1 1 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 13 1 6 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 1 0 0 0 23 24 1 0 0 0 0 25 27 2 0 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.19
Volume:	403.453
LogP:	4.156
LogD:	3.554
LogS:	-4.264
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	4.375
Fsp3:	0.36
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	1.884913581307046e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.597
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	99.3625259399414%
Volume Distribution (VD):	0.679
Pgp-substrate:	0.9933347105979919%

ADMET: Metabolism

CYP1A2-inhibitor:	0.424
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.527
CYP2C19-substrate:	0.627
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.69
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	2.314
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.632
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.546
Rat Oral Acute Toxicity:	0.725
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.375
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC242957

Natural Product ID:	NPC242957
*Common Name:**	Beilschmiedic Acid L
IUPAC Name:	n.a.
Synonyms:	Beilschmiedic Acid L
Standard InCHIKey:	NOUPIFUCBJJMRR-PJPMCNLBSA-N
Standard InCHI:	InChI=1S/C25H26O3/c26-22-14-20(25(27)28)18-12-11-17-16(19-13-21(22)24(18)23(17)19)10-6-2-5-9-15-7-3-1-4-8-15/h1-9,11-12,14,16-19,21-24,26H,10,13H2,(H,27,28)/b6-2+,9-5+/t16-,17-,18+,19+,21+,22-,23-,24+/m1/s1
SMILES:	O[C@@H]1C=C(C(=O)O)[C@H]2[C@H]3[C@H]1C[C@@H]1[C@H]3[C@@H]([C@H]1C/C=C/C=C/c1ccccc1)C=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071409
PubChem CID:	60201708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO32633	gabonese sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22758788]

☑ 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	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4400.0	nM	PMID[531689]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	11.0	ug.mL-1	PMID[531689]

☑ 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 NPC242957 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	201
0.1-0.2	861
0.2-0.3	1906
0.3-0.4	6753
0.4-0.5	16707
0.5-0.6	13680
0.6-0.7	2437
0.7-0.8	135
0.8-0.85	9
0.85-0.9	3
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC306977
1.0	High Similarity	NPC206414
1.0	High Similarity	NPC287055
0.9286	High Similarity	NPC470585
0.8739	High Similarity	NPC471935
0.8739	High Similarity	NPC471929
0.8739	High Similarity	NPC471930
0.8396	Intermediate Similarity	NPC329387
0.8396	Intermediate Similarity	NPC317280
0.8189	Intermediate Similarity	NPC471913
0.8148	Intermediate Similarity	NPC7435
0.8073	Intermediate Similarity	NPC264728
0.8036	Intermediate Similarity	NPC85560
0.8036	Intermediate Similarity	NPC244933
0.7966	Intermediate Similarity	NPC471936
0.7966	Intermediate Similarity	NPC471928
0.7966	Intermediate Similarity	NPC471925
0.7966	Intermediate Similarity	NPC471924
0.7963	Intermediate Similarity	NPC251579
0.7963	Intermediate Similarity	NPC133135
0.7946	Intermediate Similarity	NPC321670
0.7899	Intermediate Similarity	NPC471926
0.789	Intermediate Similarity	NPC120393
0.7886	Intermediate Similarity	NPC140118
0.7886	Intermediate Similarity	NPC12881
0.7881	Intermediate Similarity	NPC9274
0.787	Intermediate Similarity	NPC469893
0.7857	Intermediate Similarity	NPC329282
0.7798	Intermediate Similarity	NPC469891
0.7798	Intermediate Similarity	NPC469890
0.7798	Intermediate Similarity	NPC469892
0.7798	Intermediate Similarity	NPC289201
0.7795	Intermediate Similarity	NPC475138
0.7778	Intermediate Similarity	NPC470253
0.7739	Intermediate Similarity	NPC475282
0.7734	Intermediate Similarity	NPC72915
0.7719	Intermediate Similarity	NPC185763
0.7719	Intermediate Similarity	NPC37914
0.7719	Intermediate Similarity	NPC83409
0.7719	Intermediate Similarity	NPC94751
0.7719	Intermediate Similarity	NPC142326
0.7714	Intermediate Similarity	NPC249889
0.7714	Intermediate Similarity	NPC193843
0.7692	Intermediate Similarity	NPC471188
0.7692	Intermediate Similarity	NPC203486
0.7667	Intermediate Similarity	NPC212891
0.7667	Intermediate Similarity	NPC470820
0.7664	Intermediate Similarity	NPC475059
0.7664	Intermediate Similarity	NPC475023
0.7652	Intermediate Similarity	NPC249811
0.7647	Intermediate Similarity	NPC476357
0.7642	Intermediate Similarity	NPC310236
0.7623	Intermediate Similarity	NPC472708
0.7615	Intermediate Similarity	NPC206764
0.7611	Intermediate Similarity	NPC247976
0.7607	Intermediate Similarity	NPC95126
0.7607	Intermediate Similarity	NPC265513
0.7607	Intermediate Similarity	NPC133308
0.7607	Intermediate Similarity	NPC475002
0.7603	Intermediate Similarity	NPC152812
0.7593	Intermediate Similarity	NPC475057
0.7591	Intermediate Similarity	NPC247221
0.7589	Intermediate Similarity	NPC133809
0.7589	Intermediate Similarity	NPC136810
0.7589	Intermediate Similarity	NPC225079
0.7589	Intermediate Similarity	NPC469481
0.7589	Intermediate Similarity	NPC128248
0.7561	Intermediate Similarity	NPC474222
0.7561	Intermediate Similarity	NPC133389
0.7561	Intermediate Similarity	NPC475804
0.7561	Intermediate Similarity	NPC234337
0.7561	Intermediate Similarity	NPC183339
0.7559	Intermediate Similarity	NPC190849
0.7559	Intermediate Similarity	NPC171007
0.7544	Intermediate Similarity	NPC472222
0.7544	Intermediate Similarity	NPC472221
0.7542	Intermediate Similarity	NPC66208
0.7522	Intermediate Similarity	NPC304873
0.7519	Intermediate Similarity	NPC472388
0.7519	Intermediate Similarity	NPC49272
0.75	Intermediate Similarity	NPC186933
0.75	Intermediate Similarity	NPC472981
0.75	Intermediate Similarity	NPC112903
0.748	Intermediate Similarity	NPC275576
0.748	Intermediate Similarity	NPC470816
0.7479	Intermediate Similarity	NPC93287
0.7478	Intermediate Similarity	NPC471186
0.7458	Intermediate Similarity	NPC474057
0.7456	Intermediate Similarity	NPC255676
0.7456	Intermediate Similarity	NPC329556
0.7442	Intermediate Similarity	NPC225103
0.744	Intermediate Similarity	NPC369
0.744	Intermediate Similarity	NPC293831
0.7436	Intermediate Similarity	NPC318327
0.7424	Intermediate Similarity	NPC48929
0.7424	Intermediate Similarity	NPC126516
0.7422	Intermediate Similarity	NPC169913
0.7422	Intermediate Similarity	NPC477365
0.7419	Intermediate Similarity	NPC133302
0.7417	Intermediate Similarity	NPC294458
0.7417	Intermediate Similarity	NPC196673
0.7414	Intermediate Similarity	NPC100767
0.7414	Intermediate Similarity	NPC477251
0.7411	Intermediate Similarity	NPC179411
0.7404	Intermediate Similarity	NPC44830
0.7402	Intermediate Similarity	NPC471927
0.7388	Intermediate Similarity	NPC243893
0.7385	Intermediate Similarity	NPC473443
0.7381	Intermediate Similarity	NPC474159
0.7381	Intermediate Similarity	NPC474254
0.7368	Intermediate Similarity	NPC25458
0.7364	Intermediate Similarity	NPC477370
0.7355	Intermediate Similarity	NPC274839
0.7355	Intermediate Similarity	NPC221275
0.7355	Intermediate Similarity	NPC215419
0.7355	Intermediate Similarity	NPC217111
0.735	Intermediate Similarity	NPC20485
0.735	Intermediate Similarity	NPC211439
0.7345	Intermediate Similarity	NPC221825
0.7345	Intermediate Similarity	NPC217621
0.7344	Intermediate Similarity	NPC477366
0.7339	Intermediate Similarity	NPC202015
0.7339	Intermediate Similarity	NPC141607
0.7339	Intermediate Similarity	NPC187725
0.7339	Intermediate Similarity	NPC204784
0.7333	Intermediate Similarity	NPC477592
0.7333	Intermediate Similarity	NPC128368
0.7328	Intermediate Similarity	NPC471133
0.7328	Intermediate Similarity	NPC105899
0.7323	Intermediate Similarity	NPC85511
0.7323	Intermediate Similarity	NPC470815
0.7321	Intermediate Similarity	NPC226041
0.7317	Intermediate Similarity	NPC45794
0.7302	Intermediate Similarity	NPC269923
0.7302	Intermediate Similarity	NPC18785
0.7302	Intermediate Similarity	NPC167323
0.7293	Intermediate Similarity	NPC475627
0.7293	Intermediate Similarity	NPC18982
0.7293	Intermediate Similarity	NPC475346
0.7293	Intermediate Similarity	NPC329913
0.7293	Intermediate Similarity	NPC322503
0.7293	Intermediate Similarity	NPC470143
0.7293	Intermediate Similarity	NPC475457
0.7287	Intermediate Similarity	NPC473220
0.7287	Intermediate Similarity	NPC470753
0.728	Intermediate Similarity	NPC474223
0.728	Intermediate Similarity	NPC475827
0.7279	Intermediate Similarity	NPC234548
0.7279	Intermediate Similarity	NPC473440
0.7279	Intermediate Similarity	NPC248287
0.7273	Intermediate Similarity	NPC471721
0.7273	Intermediate Similarity	NPC80599
0.7265	Intermediate Similarity	NPC51174
0.7259	Intermediate Similarity	NPC262324
0.7258	Intermediate Similarity	NPC318173
0.7258	Intermediate Similarity	NPC472698
0.7258	Intermediate Similarity	NPC472697
0.7257	Intermediate Similarity	NPC160548
0.7257	Intermediate Similarity	NPC229242
0.7257	Intermediate Similarity	NPC166745
0.7257	Intermediate Similarity	NPC175852
0.7257	Intermediate Similarity	NPC210529
0.7257	Intermediate Similarity	NPC235464
0.7252	Intermediate Similarity	NPC82712
0.7252	Intermediate Similarity	NPC131684
0.725	Intermediate Similarity	NPC280789
0.725	Intermediate Similarity	NPC218855
0.725	Intermediate Similarity	NPC471189
0.7248	Intermediate Similarity	NPC26224
0.7248	Intermediate Similarity	NPC274455
0.7248	Intermediate Similarity	NPC70940
0.7248	Intermediate Similarity	NPC86670
0.7241	Intermediate Similarity	NPC19136
0.7241	Intermediate Similarity	NPC249067
0.7239	Intermediate Similarity	NPC471864
0.7236	Intermediate Similarity	NPC158157
0.7234	Intermediate Similarity	NPC472937
0.7234	Intermediate Similarity	NPC472936
0.7234	Intermediate Similarity	NPC472938
0.7232	Intermediate Similarity	NPC261947
0.7231	Intermediate Similarity	NPC115797
0.7231	Intermediate Similarity	NPC116057
0.7231	Intermediate Similarity	NPC51448
0.7222	Intermediate Similarity	NPC50872
0.7222	Intermediate Similarity	NPC477693
0.7222	Intermediate Similarity	NPC477704
0.7218	Intermediate Similarity	NPC15850
0.7213	Intermediate Similarity	NPC306740
0.7213	Intermediate Similarity	NPC93181
0.7209	Intermediate Similarity	NPC470765
0.7209	Intermediate Similarity	NPC470818
0.7209	Intermediate Similarity	NPC477363
0.7209	Intermediate Similarity	NPC137416
0.7197	Intermediate Similarity	NPC470278
0.719	Intermediate Similarity	NPC272524
0.719	Intermediate Similarity	NPC477475
0.719	Intermediate Similarity	NPC477476
0.7188	Intermediate Similarity	NPC318067
0.7188	Intermediate Similarity	NPC477362
0.7188	Intermediate Similarity	NPC328107

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 NPC242957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	712
0.2-0.3	1377
0.3-0.4	3018
0.4-0.5	2495
0.5-0.6	1129
0.6-0.7	208
0.7-0.8	23
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
0.7931	Intermediate Similarity	NPD7094	Approved
0.7931	Intermediate Similarity	NPD6858	Approved
0.7928	Intermediate Similarity	NPD6647	Phase 2
0.785	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2066	Phase 3
0.7611	Intermediate Similarity	NPD5765	Approved
0.7544	Intermediate Similarity	NPD5909	Discontinued
0.7541	Intermediate Similarity	NPD7009	Phase 2
0.75	Intermediate Similarity	NPD5951	Approved
0.7456	Intermediate Similarity	NPD1930	Approved
0.7456	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1929	Approved
0.7455	Intermediate Similarity	NPD1693	Approved
0.7436	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6685	Approved
0.7368	Intermediate Similarity	NPD1932	Approved
0.736	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2629	Approved
0.7317	Intermediate Similarity	NPD7610	Discontinued
0.728	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6010	Discontinued
0.7257	Intermediate Similarity	NPD9495	Approved
0.7248	Intermediate Similarity	NPD1086	Approved
0.7248	Intermediate Similarity	NPD1090	Approved
0.7248	Intermediate Similarity	NPD1089	Approved
0.7241	Intermediate Similarity	NPD1237	Approved
0.7212	Intermediate Similarity	NPD226	Approved
0.7179	Intermediate Similarity	NPD5048	Discontinued
0.7167	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD800	Approved
0.7156	Intermediate Similarity	NPD5347	Phase 2
0.7156	Intermediate Similarity	NPD5346	Phase 2
0.7143	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2329	Discontinued
0.7143	Intermediate Similarity	NPD7961	Discontinued
0.713	Intermediate Similarity	NPD4793	Discontinued
0.7121	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7008	Discontinued
0.7117	Intermediate Similarity	NPD1088	Approved
0.7107	Intermediate Similarity	NPD6912	Phase 3
0.7099	Intermediate Similarity	NPD5736	Approved
0.7091	Intermediate Similarity	NPD3672	Approved
0.7091	Intermediate Similarity	NPD3673	Approved
0.7027	Intermediate Similarity	NPD1239	Approved
0.7023	Intermediate Similarity	NPD6085	Phase 2
0.7023	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3019	Approved
0.6972	Remote Similarity	NPD1087	Approved
0.6964	Remote Similarity	NPD7631	Approved
0.6937	Remote Similarity	NPD9256	Approved
0.6937	Remote Similarity	NPD9258	Approved
0.693	Remote Similarity	NPD1989	Approved
0.6923	Remote Similarity	NPD227	Approved
0.6923	Remote Similarity	NPD225	Approved
0.6917	Remote Similarity	NPD7055	Discontinued
0.6916	Remote Similarity	NPD3971	Phase 1
0.6916	Remote Similarity	NPD9491	Approved
0.6897	Remote Similarity	NPD7239	Suspended
0.6897	Remote Similarity	NPD7798	Approved
0.6884	Remote Similarity	NPD7305	Phase 1
0.6875	Remote Similarity	NPD7609	Phase 3
0.687	Remote Similarity	NPD3495	Discontinued
0.687	Remote Similarity	NPD1566	Phase 3
0.687	Remote Similarity	NPD1565	Approved
0.687	Remote Similarity	NPD1564	Approved
0.6864	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7084	Phase 3
0.6842	Remote Similarity	NPD6049	Phase 2
0.6814	Remote Similarity	NPD1508	Approved
0.6803	Remote Similarity	NPD2067	Discontinued
0.6803	Remote Similarity	NPD1317	Discontinued
0.68	Remote Similarity	NPD4766	Approved
0.6789	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5618	Discontinued
0.6759	Remote Similarity	NPD6273	Approved
0.6746	Remote Similarity	NPD3317	Approved
0.6744	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5279	Phase 3
0.6721	Remote Similarity	NPD2182	Approved
0.672	Remote Similarity	NPD2650	Approved
0.672	Remote Similarity	NPD2652	Approved
0.6719	Remote Similarity	NPD4479	Discontinued
0.6719	Remote Similarity	NPD7741	Discontinued
0.6719	Remote Similarity	NPD3091	Approved
0.6718	Remote Similarity	NPD4878	Approved
0.6715	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD650	Approved
0.6643	Remote Similarity	NPD8166	Discontinued
0.6642	Remote Similarity	NPD7715	Approved
0.6642	Remote Similarity	NPD7714	Approved
0.6641	Remote Similarity	NPD6065	Approved
0.6638	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD1843	Approved
0.6635	Remote Similarity	NPD9716	Approved
0.6615	Remote Similarity	NPD5305	Approved
0.6615	Remote Similarity	NPD5306	Approved
0.6613	Remote Similarity	NPD3644	Approved
0.6613	Remote Similarity	NPD3643	Approved
0.6613	Remote Similarity	NPD3642	Approved
0.661	Remote Similarity	NPD1238	Approved
0.6609	Remote Similarity	NPD1563	Approved
0.6609	Remote Similarity	NPD1202	Approved
0.6591	Remote Similarity	NPD6637	Approved
0.6587	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5281	Approved
0.6579	Remote Similarity	NPD5284	Approved
0.6579	Remote Similarity	NPD7057	Phase 3
0.6579	Remote Similarity	NPD7058	Phase 2
0.6577	Remote Similarity	NPD9259	Approved
0.6577	Remote Similarity	NPD9257	Approved
0.6565	Remote Similarity	NPD3023	Approved
0.6565	Remote Similarity	NPD4879	Approved
0.6565	Remote Similarity	NPD3026	Approved
0.6557	Remote Similarity	NPD467	Phase 1
0.6542	Remote Similarity	NPD9490	Approved
0.6541	Remote Similarity	NPD5157	Phase 1
0.6541	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5159	Phase 2
0.6538	Remote Similarity	NPD3025	Approved
0.6538	Remote Similarity	NPD3024	Approved
0.6535	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD164	Approved
0.6525	Remote Similarity	NPD5926	Approved
0.6525	Remote Similarity	NPD253	Approved
0.6515	Remote Similarity	NPD2611	Approved
0.6515	Remote Similarity	NPD3131	Approved
0.6515	Remote Similarity	NPD4218	Approved
0.6515	Remote Similarity	NPD4217	Approved
0.6515	Remote Similarity	NPD3092	Approved
0.6515	Remote Similarity	NPD2609	Approved
0.6515	Remote Similarity	NPD2612	Approved
0.6515	Remote Similarity	NPD4807	Approved
0.6515	Remote Similarity	NPD4215	Approved
0.6515	Remote Similarity	NPD4216	Approved
0.6515	Remote Similarity	NPD4806	Approved
0.6515	Remote Similarity	NPD2610	Approved
0.6515	Remote Similarity	NPD3132	Approved
0.6515	Remote Similarity	NPD2608	Approved
0.65	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2345	Approved
0.6489	Remote Similarity	NPD3095	Discontinued
0.6484	Remote Similarity	NPD4198	Discontinued
0.6483	Remote Similarity	NPD7295	Approved
0.6475	Remote Similarity	NPD4140	Approved
0.6471	Remote Similarity	NPD3663	Approved
0.6471	Remote Similarity	NPD3664	Approved
0.6471	Remote Similarity	NPD6404	Discontinued
0.6471	Remote Similarity	NPD3661	Approved
0.6471	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3662	Phase 3
0.6457	Remote Similarity	NPD3598	Phase 3
0.6449	Remote Similarity	NPD3764	Approved
0.6444	Remote Similarity	NPD2797	Approved
0.6439	Remote Similarity	NPD4106	Approved
0.6439	Remote Similarity	NPD4135	Approved
0.6439	Remote Similarity	NPD4136	Approved
0.6435	Remote Similarity	NPD6079	Approved
0.6434	Remote Similarity	NPD3797	Approved
0.6434	Remote Similarity	NPD6005	Phase 3
0.6434	Remote Similarity	NPD6002	Phase 3
0.6434	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6004	Phase 3
0.6429	Remote Similarity	NPD9508	Approved
0.6429	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7003	Approved
0.6404	Remote Similarity	NPD689	Discontinued
0.64	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3133	Approved
0.6396	Remote Similarity	NPD3666	Approved
0.6396	Remote Similarity	NPD3665	Phase 1
0.6391	Remote Similarity	NPD1201	Approved
0.6378	Remote Similarity	NPD5277	Phase 2
0.6377	Remote Similarity	NPD6966	Discovery
0.6371	Remote Similarity	NPD6406	Approved
0.637	Remote Similarity	NPD1283	Approved
0.637	Remote Similarity	NPD1876	Approved
0.637	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5406	Approved
0.6364	Remote Similarity	NPD5408	Approved
0.6364	Remote Similarity	NPD5404	Approved
0.6364	Remote Similarity	NPD5405	Approved
0.6364	Remote Similarity	NPD4199	Phase 3
0.6364	Remote Similarity	NPD7137	Phase 2
0.635	Remote Similarity	NPD5204	Approved
0.6336	Remote Similarity	NPD3798	Phase 3
0.6325	Remote Similarity	NPD1066	Discontinued
0.6324	Remote Similarity	NPD3094	Phase 2
0.6324	Remote Similarity	NPD2625	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