NPASS Compound

Structure

NPC15838 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 1.3003 -2.2836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1516 -1.3104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8569 -0.3548 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 2.9360 -2.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9332 -2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2558 -1.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4965 -1.8209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2018 -0.8653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1767 -1.0879 0.0000 C 0 0 0 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 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 10 2 1 1 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 7 1 1 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	336.075
LogP:	4.281
LogD:	3.469
LogS:	-4.214
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	4.491
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.68
MDCK Permeability:	1.4503005331789609e-05
Pgp-inhibitor:	0.289
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.718
30% Bioavailability (F30%):	0.562

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.604
Plasma Protein Binding (PPB):	98.30753326416016%
Volume Distribution (VD):	1.713
Pgp-substrate:	1.3799686431884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	1.48
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.443
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.049
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: NPC15838

Natural Product ID:	NPC15838
*Common Name:**	Sikkimenoid D
IUPAC Name:	n.a.
Synonyms:	Sikkimenoid D
Standard InCHIKey:	AKYCTHTXCPVVOB-BMIKURLMSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-9-6-7-12-16(19(12,3)4)14-10(2)17(21)11-8-20(5,23)18(22)15(11)13(9)14/h10,12-14,16,23H,1,6-8H2,2-5H3/t10-,12-,13+,14-,16-,20+/m0/s1
SMILES:	C=C1CC[C@H]2[C@@H]([C@H]3[C@H](C)C(=O)C4=C([C@H]13)C(=O)[C@@](C)(C4)O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334874
PubChem CID:	71579216
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003546] Jatropholane and crotopholane 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
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327832]
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26756779]
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[520797]

☑ 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 NPC15838 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	212
0.1-0.2	1906
0.2-0.3	10247
0.3-0.4	15971
0.4-0.5	7747
0.5-0.6	5342
0.6-0.7	1222
0.7-0.8	44
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC132629
0.8228	Intermediate Similarity	NPC151045
0.8228	Intermediate Similarity	NPC246722
0.8046	Intermediate Similarity	NPC144258
0.7976	Intermediate Similarity	NPC19443
0.7935	Intermediate Similarity	NPC233118
0.7901	Intermediate Similarity	NPC144627
0.7816	Intermediate Similarity	NPC193347
0.7791	Intermediate Similarity	NPC108955
0.7738	Intermediate Similarity	NPC92080
0.7701	Intermediate Similarity	NPC136150
0.7701	Intermediate Similarity	NPC55869
0.764	Intermediate Similarity	NPC237712
0.7609	Intermediate Similarity	NPC326627
0.7609	Intermediate Similarity	NPC310010
0.7558	Intermediate Similarity	NPC476808
0.7558	Intermediate Similarity	NPC275494
0.7558	Intermediate Similarity	NPC30321
0.7558	Intermediate Similarity	NPC471409
0.7556	Intermediate Similarity	NPC474853
0.7556	Intermediate Similarity	NPC123319
0.7556	Intermediate Similarity	NPC142649
0.7556	Intermediate Similarity	NPC36350
0.7556	Intermediate Similarity	NPC179006
0.7556	Intermediate Similarity	NPC311702
0.7556	Intermediate Similarity	NPC94531
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC474854
0.75	Intermediate Similarity	NPC225515
0.7473	Intermediate Similarity	NPC6247
0.7473	Intermediate Similarity	NPC472479
0.7473	Intermediate Similarity	NPC472488
0.7473	Intermediate Similarity	NPC327115
0.7473	Intermediate Similarity	NPC203795
0.7473	Intermediate Similarity	NPC94666
0.7444	Intermediate Similarity	NPC472480
0.7442	Intermediate Similarity	NPC266193
0.7442	Intermediate Similarity	NPC257666
0.7442	Intermediate Similarity	NPC266124
0.7419	Intermediate Similarity	NPC76879
0.7419	Intermediate Similarity	NPC119416
0.7416	Intermediate Similarity	NPC129080
0.7416	Intermediate Similarity	NPC477271
0.7416	Intermediate Similarity	NPC477269
0.7416	Intermediate Similarity	NPC469325
0.7416	Intermediate Similarity	NPC477270
0.7412	Intermediate Similarity	NPC251435
0.7386	Intermediate Similarity	NPC2482
0.7386	Intermediate Similarity	NPC476809
0.7368	Intermediate Similarity	NPC12722
0.7363	Intermediate Similarity	NPC8518
0.7363	Intermediate Similarity	NPC241512
0.7363	Intermediate Similarity	NPC6185
0.7363	Intermediate Similarity	NPC33663
0.7363	Intermediate Similarity	NPC263997
0.7363	Intermediate Similarity	NPC469993
0.7363	Intermediate Similarity	NPC132228
0.7363	Intermediate Similarity	NPC469948
0.7356	Intermediate Similarity	NPC23778
0.7356	Intermediate Similarity	NPC74410
0.7333	Intermediate Similarity	NPC470015
0.7333	Intermediate Similarity	NPC105803
0.7333	Intermediate Similarity	NPC470165
0.7333	Intermediate Similarity	NPC168188
0.7333	Intermediate Similarity	NPC472492
0.7333	Intermediate Similarity	NPC53733
0.7326	Intermediate Similarity	NPC470525
0.7326	Intermediate Similarity	NPC186554
0.7326	Intermediate Similarity	NPC180886
0.7326	Intermediate Similarity	NPC182848
0.7326	Intermediate Similarity	NPC76966
0.7312	Intermediate Similarity	NPC471941
0.7303	Intermediate Similarity	NPC226068
0.7303	Intermediate Similarity	NPC121984
0.7303	Intermediate Similarity	NPC189237
0.7292	Intermediate Similarity	NPC217624
0.7292	Intermediate Similarity	NPC181393
0.7283	Intermediate Similarity	NPC474733
0.7283	Intermediate Similarity	NPC20688
0.7283	Intermediate Similarity	NPC31564
0.7283	Intermediate Similarity	NPC474778
0.7283	Intermediate Similarity	NPC51014
0.7283	Intermediate Similarity	NPC145879
0.7283	Intermediate Similarity	NPC474732
0.7273	Intermediate Similarity	NPC215843
0.7273	Intermediate Similarity	NPC477371
0.7273	Intermediate Similarity	NPC27817
0.7273	Intermediate Similarity	NPC472490
0.7273	Intermediate Similarity	NPC192329
0.7273	Intermediate Similarity	NPC229204
0.7262	Intermediate Similarity	NPC469737
0.7262	Intermediate Similarity	NPC84790
0.7253	Intermediate Similarity	NPC85774
0.7253	Intermediate Similarity	NPC473246
0.7253	Intermediate Similarity	NPC58841
0.7253	Intermediate Similarity	NPC161423
0.7253	Intermediate Similarity	NPC214043
0.7253	Intermediate Similarity	NPC329043
0.7253	Intermediate Similarity	NPC321187
0.7253	Intermediate Similarity	NPC227064
0.7253	Intermediate Similarity	NPC209882
0.7245	Intermediate Similarity	NPC472689
0.7245	Intermediate Similarity	NPC472073
0.7245	Intermediate Similarity	NPC43747
0.7245	Intermediate Similarity	NPC477268
0.7245	Intermediate Similarity	NPC473161
0.7245	Intermediate Similarity	NPC472690
0.7245	Intermediate Similarity	NPC477267
0.7245	Intermediate Similarity	NPC472074
0.7241	Intermediate Similarity	NPC472014
0.7241	Intermediate Similarity	NPC165711
0.7241	Intermediate Similarity	NPC34110
0.7234	Intermediate Similarity	NPC472477
0.7234	Intermediate Similarity	NPC472475
0.7234	Intermediate Similarity	NPC170775
0.7234	Intermediate Similarity	NPC477943
0.7234	Intermediate Similarity	NPC472489
0.7234	Intermediate Similarity	NPC474245
0.7222	Intermediate Similarity	NPC302661
0.7222	Intermediate Similarity	NPC133391
0.7222	Intermediate Similarity	NPC103486
0.7222	Intermediate Similarity	NPC260956
0.7222	Intermediate Similarity	NPC320514
0.7222	Intermediate Similarity	NPC238991
0.7212	Intermediate Similarity	NPC163004
0.7209	Intermediate Similarity	NPC175079
0.7209	Intermediate Similarity	NPC77501
0.7209	Intermediate Similarity	NPC114236
0.7204	Intermediate Similarity	NPC136548
0.7204	Intermediate Similarity	NPC472481
0.7204	Intermediate Similarity	NPC475740
0.7204	Intermediate Similarity	NPC471792
0.7204	Intermediate Similarity	NPC472482
0.7204	Intermediate Similarity	NPC136948
0.7204	Intermediate Similarity	NPC472484
0.7204	Intermediate Similarity	NPC58063
0.7204	Intermediate Similarity	NPC99909
0.7191	Intermediate Similarity	NPC26139
0.7191	Intermediate Similarity	NPC18955
0.7191	Intermediate Similarity	NPC472478
0.7191	Intermediate Similarity	NPC279667
0.7191	Intermediate Similarity	NPC164218
0.7191	Intermediate Similarity	NPC469637
0.7188	Intermediate Similarity	NPC125180
0.7188	Intermediate Similarity	NPC134826
0.7188	Intermediate Similarity	NPC109414
0.7184	Intermediate Similarity	NPC185
0.7174	Intermediate Similarity	NPC202868
0.7174	Intermediate Similarity	NPC79573
0.7174	Intermediate Similarity	NPC11711
0.7174	Intermediate Similarity	NPC473038
0.7174	Intermediate Similarity	NPC474218
0.7174	Intermediate Similarity	NPC474680
0.7174	Intermediate Similarity	NPC29447
0.7172	Intermediate Similarity	NPC147954
0.7159	Intermediate Similarity	NPC475994
0.7159	Intermediate Similarity	NPC207772
0.7159	Intermediate Similarity	NPC189485
0.7158	Intermediate Similarity	NPC474209
0.7158	Intermediate Similarity	NPC475823
0.7158	Intermediate Similarity	NPC472476
0.7158	Intermediate Similarity	NPC129913
0.7157	Intermediate Similarity	NPC72255
0.7143	Intermediate Similarity	NPC477373
0.7143	Intermediate Similarity	NPC62214
0.7143	Intermediate Similarity	NPC163020
0.7143	Intermediate Similarity	NPC477852
0.7143	Intermediate Similarity	NPC102197
0.7143	Intermediate Similarity	NPC153036
0.7129	Intermediate Similarity	NPC163249
0.7129	Intermediate Similarity	NPC87351
0.7128	Intermediate Similarity	NPC320665
0.7128	Intermediate Similarity	NPC472483
0.7128	Intermediate Similarity	NPC471722
0.7128	Intermediate Similarity	NPC190718
0.7128	Intermediate Similarity	NPC476796
0.7128	Intermediate Similarity	NPC117122
0.7128	Intermediate Similarity	NPC474677
0.7128	Intermediate Similarity	NPC472802
0.7126	Intermediate Similarity	NPC263582
0.7126	Intermediate Similarity	NPC472305
0.7126	Intermediate Similarity	NPC151622
0.7126	Intermediate Similarity	NPC7629
0.7126	Intermediate Similarity	NPC1254
0.7113	Intermediate Similarity	NPC196485
0.7113	Intermediate Similarity	NPC245972
0.7111	Intermediate Similarity	NPC472684
0.7111	Intermediate Similarity	NPC150506
0.7111	Intermediate Similarity	NPC147066
0.7111	Intermediate Similarity	NPC201912
0.7111	Intermediate Similarity	NPC471898
0.7111	Intermediate Similarity	NPC44963
0.7111	Intermediate Similarity	NPC278459
0.7111	Intermediate Similarity	NPC473217
0.7111	Intermediate Similarity	NPC38350
0.7111	Intermediate Similarity	NPC474085
0.71	Intermediate Similarity	NPC474720
0.71	Intermediate Similarity	NPC112167
0.7097	Intermediate Similarity	NPC472491
0.7097	Intermediate Similarity	NPC472494

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 NPC15838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	2608
0.2-0.3	4197
0.3-0.4	1548
0.4-0.5	323
0.5-0.6	204
0.6-0.7	46
0.7-0.8	2
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
0.8046	Intermediate Similarity	NPD4197	Approved
0.7955	Intermediate Similarity	NPD5329	Approved
0.7865	Intermediate Similarity	NPD5280	Approved
0.7865	Intermediate Similarity	NPD5690	Phase 2
0.7865	Intermediate Similarity	NPD4694	Approved
0.7816	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4221	Approved
0.7766	Intermediate Similarity	NPD4629	Approved
0.7766	Intermediate Similarity	NPD5210	Approved
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7586	Intermediate Similarity	NPD4695	Discontinued
0.7558	Intermediate Similarity	NPD3617	Approved
0.7553	Intermediate Similarity	NPD5133	Approved
0.7526	Intermediate Similarity	NPD5696	Approved
0.7473	Intermediate Similarity	NPD4138	Approved
0.7473	Intermediate Similarity	NPD4693	Phase 3
0.7473	Intermediate Similarity	NPD4690	Approved
0.7473	Intermediate Similarity	NPD4689	Approved
0.7473	Intermediate Similarity	NPD5205	Approved
0.7473	Intermediate Similarity	NPD4688	Approved
0.73	Intermediate Similarity	NPD5091	Approved
0.7283	Intermediate Similarity	NPD5279	Phase 3
0.7283	Intermediate Similarity	NPD4623	Approved
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7263	Intermediate Similarity	NPD5284	Approved
0.7263	Intermediate Similarity	NPD5281	Approved
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD5695	Phase 3
0.7174	Intermediate Similarity	NPD1696	Phase 3
0.7128	Intermediate Similarity	NPD4518	Approved
0.7111	Intermediate Similarity	NPD4692	Approved
0.7111	Intermediate Similarity	NPD4139	Approved
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD4195	Approved
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7065	Intermediate Similarity	NPD4786	Approved
0.7053	Intermediate Similarity	NPD6904	Approved
0.7053	Intermediate Similarity	NPD6080	Approved
0.7053	Intermediate Similarity	NPD6673	Approved
0.7033	Intermediate Similarity	NPD3667	Approved
0.701	Intermediate Similarity	NPD4202	Approved
0.6979	Remote Similarity	NPD4096	Approved
0.6979	Remote Similarity	NPD5692	Phase 3
0.697	Remote Similarity	NPD4697	Phase 3
0.6951	Remote Similarity	NPD7341	Phase 2
0.6939	Remote Similarity	NPD6001	Approved
0.6931	Remote Similarity	NPD4696	Approved
0.6931	Remote Similarity	NPD5286	Approved
0.6931	Remote Similarity	NPD4700	Approved
0.6931	Remote Similarity	NPD5285	Approved
0.6915	Remote Similarity	NPD6098	Approved
0.6907	Remote Similarity	NPD5693	Phase 1
0.6907	Remote Similarity	NPD6050	Approved
0.6907	Remote Similarity	NPD5694	Approved
0.6875	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7331	Phase 2
0.6863	Remote Similarity	NPD5223	Approved
0.6804	Remote Similarity	NPD5207	Approved
0.68	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5222	Approved
0.68	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5226	Approved
0.6796	Remote Similarity	NPD4633	Approved
0.6796	Remote Similarity	NPD5224	Approved
0.6796	Remote Similarity	NPD5225	Approved
0.6796	Remote Similarity	NPD5211	Phase 2
0.6774	Remote Similarity	NPD4788	Approved
0.6771	Remote Similarity	NPD6672	Approved
0.6771	Remote Similarity	NPD5737	Approved
0.6771	Remote Similarity	NPD5208	Approved
0.6768	Remote Similarity	NPD5282	Discontinued
0.6744	Remote Similarity	NPD4747	Approved
0.6735	Remote Similarity	NPD6079	Approved
0.6733	Remote Similarity	NPD5173	Approved
0.6733	Remote Similarity	NPD5959	Approved
0.6731	Remote Similarity	NPD4754	Approved
0.6731	Remote Similarity	NPD5174	Approved
0.6731	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5141	Approved
0.6628	Remote Similarity	NPD4137	Phase 3
0.6604	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.6604	Remote Similarity	NPD4767	Approved
0.6574	Remote Similarity	NPD6372	Approved
0.6574	Remote Similarity	NPD6373	Approved
0.6562	Remote Similarity	NPD5330	Approved
0.6562	Remote Similarity	NPD7146	Approved
0.6562	Remote Similarity	NPD7521	Approved
0.6562	Remote Similarity	NPD6409	Approved
0.6562	Remote Similarity	NPD6684	Approved
0.6562	Remote Similarity	NPD7334	Approved
0.6552	Remote Similarity	NPD4691	Approved
0.6542	Remote Similarity	NPD5701	Approved
0.6542	Remote Similarity	NPD6614	Approved
0.6542	Remote Similarity	NPD5697	Approved
0.6535	Remote Similarity	NPD5654	Approved
0.6526	Remote Similarity	NPD3668	Phase 3
0.6517	Remote Similarity	NPD4784	Approved
0.6517	Remote Similarity	NPD5733	Approved
0.6517	Remote Similarity	NPD4785	Approved
0.6517	Remote Similarity	NPD4687	Approved
0.6506	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4729	Approved
0.6481	Remote Similarity	NPD6899	Approved
0.6481	Remote Similarity	NPD6011	Approved
0.6481	Remote Similarity	NPD5128	Approved
0.6481	Remote Similarity	NPD6881	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6481	Remote Similarity	NPD4730	Approved
0.6477	Remote Similarity	NPD5276	Approved
0.6477	Remote Similarity	NPD4243	Approved
0.6455	Remote Similarity	NPD6650	Approved
0.6455	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6012	Approved
0.6422	Remote Similarity	NPD6014	Approved
0.6422	Remote Similarity	NPD6013	Approved
0.64	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD5169	Approved
0.6364	Remote Similarity	NPD6371	Approved
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD5251	Approved
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6333	Remote Similarity	NPD4058	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6311	Remote Similarity	NPD7614	Phase 1
0.6306	Remote Similarity	NPD5127	Approved
0.6306	Remote Similarity	NPD8130	Phase 1
0.6306	Remote Similarity	NPD5215	Approved
0.6306	Remote Similarity	NPD5217	Approved
0.6306	Remote Similarity	NPD5216	Approved
0.6306	Remote Similarity	NPD6847	Approved
0.6306	Remote Similarity	NPD6869	Approved
0.6306	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6617	Approved
0.6296	Remote Similarity	NPD6008	Approved
0.6277	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7748	Approved
0.6264	Remote Similarity	NPD4190	Phase 3
0.6264	Remote Similarity	NPD5275	Approved
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD7902	Approved
0.622	Remote Similarity	NPD287	Approved
0.6214	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4632	Approved
0.6182	Remote Similarity	NPD5168	Approved
0.614	Remote Similarity	NPD5167	Approved
0.6136	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6052	Approved
0.6092	Remote Similarity	NPD3704	Approved
0.6087	Remote Similarity	NPD7339	Approved
0.6087	Remote Similarity	NPD6274	Approved
0.6087	Remote Similarity	NPD6942	Approved
0.6042	Remote Similarity	NPD5369	Approved
0.604	Remote Similarity	NPD1695	Approved
0.6034	Remote Similarity	NPD6009	Approved
0.6034	Remote Similarity	NPD7115	Discovery
0.6034	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD4789	Approved
0.5983	Remote Similarity	NPD6314	Approved
0.5983	Remote Similarity	NPD6313	Approved
0.5983	Remote Similarity	NPD6335	Approved
0.5981	Remote Similarity	NPD6404	Discontinued
0.598	Remote Similarity	NPD5785	Approved
0.5979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD6924	Approved
0.5977	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7900	Approved
0.5962	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1694	Approved
0.596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5363	Approved
0.5955	Remote Similarity	NPD5360	Phase 3
0.5955	Remote Similarity	NPD5361	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data