NPASS Compound

Structure

NPC31019 OpenBabel07101718292D 28 30 0 0 1 0 0 0 0 0999 V2000 9.8455 -2.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4388 -1.9202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4443 -1.8156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0375 -0.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0430 -0.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6363 0.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6417 0.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2350 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2405 1.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8337 2.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8392 2.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0759 -0.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -0.2749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2514 1.4476 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 -1.1885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2569 1.5522 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 1 0 0 0 22 11 1 6 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 17 1 6 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.28
Volume:	425.242
LogP:	5.559
LogD:	4.083
LogS:	-5.967
# Rotatable Bonds:	10
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.508
Synthetic Accessibility Score:	4.753
Fsp3:	0.792
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:	-4.746
MDCK Permeability:	3.4895499993581325e-05
Pgp-inhibitor:	0.521
Pgp-substrate:	0.169
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.578
Plasma Protein Binding (PPB):	97.97269439697266%
Volume Distribution (VD):	1.531
Pgp-substrate:	1.269587755203247%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.437
CYP2C19-inhibitor:	0.836
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.667
CYP2C9-substrate:	0.458
CYP2D6-inhibitor:	0.805
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.728

ADMET: Excretion

Clearance (CL):	11.134
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.628
Human Hepatotoxicity (H-HT):	0.711
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.358
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.982
Carcinogencity:	0.885
Eye Corrosion:	0.338
Eye Irritation:	0.917
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC31019

Natural Product ID:	NPC31019
*Common Name:**	Aculeatin F
IUPAC Name:	(2R,4R,6R)-2-hydroxy-4-undecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-11-one
Synonyms:	aculeatin F
Standard InCHIKey:	PDRKXTBGPRXZHI-CQOQZXRMSA-N
Standard InCHI:	InChI=1S/C24H38O4/c1-2-3-4-5-6-7-8-9-10-11-22-18-21(26)19-24(27-22)17-16-23(28-24)14-12-20(25)13-15-23/h12-15,21-22,26H,2-11,16-19H2,1H3/t21-,22-,24-/m1/s1
SMILES:	CCCCCCCCCCC[C@@H]1C[C@@H](O)C[C@@]2(O1)CCC1(O2)C=CC(=O)C=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256566
PubChem CID:	24853600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.0	uM	PMID[532261]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.5	uM	PMID[532261]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.2	uM	PMID[532261]

☑ 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 NPC31019 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	142
0.1-0.2	1129
0.2-0.3	5376
0.3-0.4	12544
0.4-0.5	11860
0.5-0.6	8155
0.6-0.7	3259
0.7-0.8	221
0.8-0.85	0
0.85-0.9	3
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC2379
1.0	High Similarity	NPC263087
1.0	High Similarity	NPC106912
1.0	High Similarity	NPC27314
0.9351	High Similarity	NPC326753
0.9241	High Similarity	NPC473339
0.9241	High Similarity	NPC471552
0.8721	High Similarity	NPC471569
0.8571	High Similarity	NPC473353
0.8556	High Similarity	NPC266842
0.8022	Intermediate Similarity	NPC256368
0.7955	Intermediate Similarity	NPC313658
0.7955	Intermediate Similarity	NPC316138
0.7889	Intermediate Similarity	NPC202886
0.7857	Intermediate Similarity	NPC139712
0.7802	Intermediate Similarity	NPC477749
0.7778	Intermediate Similarity	NPC477748
0.7778	Intermediate Similarity	NPC133450
0.7727	Intermediate Similarity	NPC471494
0.7692	Intermediate Similarity	NPC177668
0.7684	Intermediate Similarity	NPC203627
0.7674	Intermediate Similarity	NPC469469
0.764	Intermediate Similarity	NPC311163
0.7629	Intermediate Similarity	NPC150463
0.7614	Intermediate Similarity	NPC266718
0.7614	Intermediate Similarity	NPC475035
0.7561	Intermediate Similarity	NPC185186
0.7561	Intermediate Similarity	NPC327383
0.7556	Intermediate Similarity	NPC199382
0.7551	Intermediate Similarity	NPC473070
0.7527	Intermediate Similarity	NPC472196
0.7527	Intermediate Similarity	NPC238090
0.7527	Intermediate Similarity	NPC472195
0.7475	Intermediate Similarity	NPC473068
0.7471	Intermediate Similarity	NPC184208
0.7471	Intermediate Similarity	NPC8538
0.7447	Intermediate Similarity	NPC159698
0.7444	Intermediate Similarity	NPC208473
0.7426	Intermediate Similarity	NPC473069
0.7412	Intermediate Similarity	NPC477203
0.74	Intermediate Similarity	NPC239961
0.7391	Intermediate Similarity	NPC471054
0.7381	Intermediate Similarity	NPC285840
0.7381	Intermediate Similarity	NPC327041
0.7363	Intermediate Similarity	NPC471055
0.7363	Intermediate Similarity	NPC471056
0.7363	Intermediate Similarity	NPC475037
0.7349	Intermediate Similarity	NPC329914
0.7347	Intermediate Similarity	NPC2313
0.7347	Intermediate Similarity	NPC154132
0.7347	Intermediate Similarity	NPC475157
0.7347	Intermediate Similarity	NPC475655
0.7347	Intermediate Similarity	NPC471637
0.7347	Intermediate Similarity	NPC57586
0.734	Intermediate Similarity	NPC471483
0.7327	Intermediate Similarity	NPC109376
0.7326	Intermediate Similarity	NPC248775
0.732	Intermediate Similarity	NPC65700
0.7312	Intermediate Similarity	NPC3952
0.7312	Intermediate Similarity	NPC327253
0.7312	Intermediate Similarity	NPC118078
0.7303	Intermediate Similarity	NPC474809
0.73	Intermediate Similarity	NPC194941
0.7294	Intermediate Similarity	NPC469880
0.7294	Intermediate Similarity	NPC229655
0.7294	Intermediate Similarity	NPC477202
0.7292	Intermediate Similarity	NPC288350
0.7292	Intermediate Similarity	NPC173329
0.7283	Intermediate Similarity	NPC248312
0.7283	Intermediate Similarity	NPC106051
0.7273	Intermediate Similarity	NPC201191
0.7273	Intermediate Similarity	NPC214277
0.7273	Intermediate Similarity	NPC315731
0.7263	Intermediate Similarity	NPC25701
0.7263	Intermediate Similarity	NPC469491
0.7263	Intermediate Similarity	NPC2003
0.7255	Intermediate Similarity	NPC470024
0.7255	Intermediate Similarity	NPC224660
0.7245	Intermediate Similarity	NPC79631
0.7241	Intermediate Similarity	NPC470149
0.7241	Intermediate Similarity	NPC226226
0.7241	Intermediate Similarity	NPC180725
0.7241	Intermediate Similarity	NPC55304
0.7241	Intermediate Similarity	NPC470148
0.7238	Intermediate Similarity	NPC287075
0.7234	Intermediate Similarity	NPC476084
0.7234	Intermediate Similarity	NPC471324
0.7234	Intermediate Similarity	NPC206679
0.7234	Intermediate Similarity	NPC114172
0.7234	Intermediate Similarity	NPC476075
0.7228	Intermediate Similarity	NPC172867
0.7228	Intermediate Similarity	NPC218158
0.7222	Intermediate Similarity	NPC186155
0.7222	Intermediate Similarity	NPC160517
0.7222	Intermediate Similarity	NPC78673
0.7222	Intermediate Similarity	NPC473308
0.7222	Intermediate Similarity	NPC471301
0.7216	Intermediate Similarity	NPC278506
0.7216	Intermediate Similarity	NPC309503
0.7216	Intermediate Similarity	NPC98112
0.7216	Intermediate Similarity	NPC91695
0.7216	Intermediate Similarity	NPC70145
0.7216	Intermediate Similarity	NPC155319
0.7216	Intermediate Similarity	NPC239547
0.7216	Intermediate Similarity	NPC125551
0.7216	Intermediate Similarity	NPC91197
0.7216	Intermediate Similarity	NPC96597
0.7209	Intermediate Similarity	NPC233071
0.7209	Intermediate Similarity	NPC474026
0.72	Intermediate Similarity	NPC472750
0.72	Intermediate Similarity	NPC472747
0.72	Intermediate Similarity	NPC197736
0.7191	Intermediate Similarity	NPC471298
0.7191	Intermediate Similarity	NPC251026
0.7174	Intermediate Similarity	NPC241054
0.7172	Intermediate Similarity	NPC154127
0.7172	Intermediate Similarity	NPC280991
0.7172	Intermediate Similarity	NPC198992
0.7159	Intermediate Similarity	NPC470147
0.7159	Intermediate Similarity	NPC133226
0.7159	Intermediate Similarity	NPC100697
0.7158	Intermediate Similarity	NPC320089
0.7158	Intermediate Similarity	NPC474792
0.7158	Intermediate Similarity	NPC91654
0.7158	Intermediate Similarity	NPC320552
0.7158	Intermediate Similarity	NPC109406
0.7158	Intermediate Similarity	NPC189651
0.7158	Intermediate Similarity	NPC67398
0.7158	Intermediate Similarity	NPC159092
0.7158	Intermediate Similarity	NPC475098
0.7143	Intermediate Similarity	NPC83895
0.7143	Intermediate Similarity	NPC81483
0.7143	Intermediate Similarity	NPC329890
0.7143	Intermediate Similarity	NPC61630
0.7143	Intermediate Similarity	NPC169468
0.7143	Intermediate Similarity	NPC255592
0.7143	Intermediate Similarity	NPC40182
0.7143	Intermediate Similarity	NPC163606
0.7143	Intermediate Similarity	NPC187761
0.7143	Intermediate Similarity	NPC307517
0.7143	Intermediate Similarity	NPC261377
0.7143	Intermediate Similarity	NPC198422
0.7143	Intermediate Similarity	NPC308567
0.7143	Intermediate Similarity	NPC475034
0.7129	Intermediate Similarity	NPC472748
0.7128	Intermediate Similarity	NPC179394
0.7128	Intermediate Similarity	NPC473448
0.7128	Intermediate Similarity	NPC144133
0.7128	Intermediate Similarity	NPC473311
0.7128	Intermediate Similarity	NPC475855
0.7115	Intermediate Similarity	NPC316708
0.7113	Intermediate Similarity	NPC143446
0.7111	Intermediate Similarity	NPC471297
0.7111	Intermediate Similarity	NPC142111
0.7111	Intermediate Similarity	NPC473315
0.7111	Intermediate Similarity	NPC44261
0.7108	Intermediate Similarity	NPC476012
0.71	Intermediate Similarity	NPC223834
0.71	Intermediate Similarity	NPC238397
0.71	Intermediate Similarity	NPC471363
0.7097	Intermediate Similarity	NPC472011
0.7093	Intermediate Similarity	NPC188860
0.7093	Intermediate Similarity	NPC326661
0.7083	Intermediate Similarity	NPC474338
0.7079	Intermediate Similarity	NPC475944
0.7079	Intermediate Similarity	NPC112868
0.7079	Intermediate Similarity	NPC280367
0.7071	Intermediate Similarity	NPC477721
0.7071	Intermediate Similarity	NPC477716
0.7071	Intermediate Similarity	NPC130792
0.7065	Intermediate Similarity	NPC186332
0.7065	Intermediate Similarity	NPC47220
0.7065	Intermediate Similarity	NPC61527
0.7059	Intermediate Similarity	NPC315070
0.7059	Intermediate Similarity	NPC469960
0.7059	Intermediate Similarity	NPC472751
0.7059	Intermediate Similarity	NPC472749
0.7059	Intermediate Similarity	NPC265502
0.7059	Intermediate Similarity	NPC29389
0.7059	Intermediate Similarity	NPC82251
0.7059	Intermediate Similarity	NPC93026
0.7059	Intermediate Similarity	NPC474280
0.7053	Intermediate Similarity	NPC472010
0.7048	Intermediate Similarity	NPC470026
0.7048	Intermediate Similarity	NPC17791
0.7045	Intermediate Similarity	NPC321728
0.7041	Intermediate Similarity	NPC40812
0.7041	Intermediate Similarity	NPC475332
0.7041	Intermediate Similarity	NPC476613
0.7041	Intermediate Similarity	NPC476612
0.7033	Intermediate Similarity	NPC126518
0.703	Intermediate Similarity	NPC151516
0.703	Intermediate Similarity	NPC475889
0.703	Intermediate Similarity	NPC120009
0.703	Intermediate Similarity	NPC7613
0.703	Intermediate Similarity	NPC7644
0.703	Intermediate Similarity	NPC134270
0.703	Intermediate Similarity	NPC127933
0.7021	Intermediate Similarity	NPC470819
0.7021	Intermediate Similarity	NPC205548

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 NPC31019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1496
0.2-0.3	4355
0.3-0.4	2275
0.4-0.5	525
0.5-0.6	315
0.6-0.7	51
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD46	Approved
0.6947	Remote Similarity	NPD7838	Discovery
0.6947	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.6729	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5344	Discontinued
0.6637	Remote Similarity	NPD7503	Approved
0.6509	Remote Similarity	NPD6412	Phase 2
0.6458	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD4250	Approved
0.6408	Remote Similarity	NPD6648	Approved
0.64	Remote Similarity	NPD5282	Discontinued
0.6372	Remote Similarity	NPD7328	Approved
0.6372	Remote Similarity	NPD7327	Approved
0.6354	Remote Similarity	NPD4249	Approved
0.6348	Remote Similarity	NPD8513	Phase 3
0.6348	Remote Similarity	NPD8515	Approved
0.6348	Remote Similarity	NPD8516	Approved
0.6348	Remote Similarity	NPD8517	Approved
0.6316	Remote Similarity	NPD7516	Approved
0.6311	Remote Similarity	NPD7638	Approved
0.631	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5785	Approved
0.6261	Remote Similarity	NPD6054	Approved
0.6261	Remote Similarity	NPD8377	Approved
0.6261	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6239	Remote Similarity	NPD7642	Approved
0.6237	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD4821	Approved
0.6237	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4822	Approved
0.6237	Remote Similarity	NPD4820	Approved
0.6216	Remote Similarity	NPD6053	Discontinued
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8033	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6204	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6371	Approved
0.6176	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4225	Approved
0.6154	Remote Similarity	NPD6370	Approved
0.6146	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6117	Remote Similarity	NPD7839	Suspended
0.6111	Remote Similarity	NPD4211	Phase 1
0.6105	Remote Similarity	NPD6435	Approved
0.6102	Remote Similarity	NPD7830	Approved
0.6102	Remote Similarity	NPD7829	Approved
0.6083	Remote Similarity	NPD8074	Phase 3
0.6082	Remote Similarity	NPD5363	Approved
0.6082	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6882	Approved
0.6068	Remote Similarity	NPD6016	Approved
0.6068	Remote Similarity	NPD6015	Approved
0.605	Remote Similarity	NPD7492	Approved
0.6042	Remote Similarity	NPD7154	Phase 3
0.6042	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD7637	Suspended
0.604	Remote Similarity	NPD7983	Approved
0.6022	Remote Similarity	NPD4268	Approved
0.6022	Remote Similarity	NPD4271	Approved
0.6017	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD6059	Approved
0.595	Remote Similarity	NPD7078	Approved
0.5946	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD7736	Approved
0.5895	Remote Similarity	NPD7514	Phase 3
0.5895	Remote Similarity	NPD5368	Approved
0.5895	Remote Similarity	NPD7332	Phase 2
0.5876	Remote Similarity	NPD6110	Phase 1
0.5862	Remote Similarity	NPD6009	Approved
0.5862	Remote Similarity	NPD7500	Approved
0.5862	Remote Similarity	NPD7115	Discovery
0.5862	Remote Similarity	NPD7331	Phase 2
0.5856	Remote Similarity	NPD6881	Approved
0.5856	Remote Similarity	NPD6899	Approved
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD1695	Approved
0.5842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6101	Approved
0.5833	Remote Similarity	NPD7632	Discontinued
0.5833	Remote Similarity	NPD5369	Approved
0.5812	Remote Similarity	NPD7641	Discontinued
0.58	Remote Similarity	NPD7524	Approved
0.58	Remote Similarity	NPD7750	Discontinued
0.5798	Remote Similarity	NPD8444	Approved
0.5773	Remote Similarity	NPD5209	Approved
0.5773	Remote Similarity	NPD4270	Approved
0.5773	Remote Similarity	NPD4269	Approved
0.5773	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5697	Approved
0.5765	Remote Similarity	NPD368	Approved
0.5755	Remote Similarity	NPD6084	Phase 2
0.5755	Remote Similarity	NPD6083	Phase 2
0.5752	Remote Similarity	NPD7102	Approved
0.5752	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7290	Approved
0.5752	Remote Similarity	NPD6883	Approved
0.5745	Remote Similarity	NPD6932	Approved
0.5738	Remote Similarity	NPD8451	Approved
0.5729	Remote Similarity	NPD6931	Approved
0.5729	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6930	Phase 2
0.5728	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5362	Discontinued
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6649	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6650	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.57	Remote Similarity	NPD5786	Approved
0.5699	Remote Similarity	NPD8039	Approved
0.5691	Remote Similarity	NPD8448	Approved
0.5691	Remote Similarity	NPD8293	Discontinued
0.5688	Remote Similarity	NPD5211	Phase 2
0.5686	Remote Similarity	NPD6051	Approved
0.5684	Remote Similarity	NPD7145	Approved
0.568	Remote Similarity	NPD5956	Approved
0.5676	Remote Similarity	NPD7128	Approved
0.5676	Remote Similarity	NPD6402	Approved
0.5676	Remote Similarity	NPD6675	Approved
0.5676	Remote Similarity	NPD5739	Approved
0.567	Remote Similarity	NPD6902	Approved
0.5664	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6012	Approved
0.5664	Remote Similarity	NPD6013	Approved
0.5664	Remote Similarity	NPD6014	Approved
0.5652	Remote Similarity	NPD8297	Approved
0.5648	Remote Similarity	NPD5286	Approved
0.5648	Remote Similarity	NPD5285	Approved
0.5648	Remote Similarity	NPD4696	Approved
0.5632	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4195	Approved
0.5625	Remote Similarity	NPD6929	Approved
0.562	Remote Similarity	NPD5125	Phase 3
0.562	Remote Similarity	NPD5126	Approved
0.5603	Remote Similarity	NPD8133	Approved
0.5603	Remote Similarity	NPD4632	Approved
0.56	Remote Similarity	NPD1696	Phase 3

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