NPASS Compound

Structure

NPC151045 OpenBabel07101719242D 22 25 0 0 1 0 0 0 0 0999 V2000 -3.8764 -1.1957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1767 1.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 2.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6802 0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2407 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2435 -1.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5889 1.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9209 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1767 1.0879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9058 1.5879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6379 1.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7718 0.0879 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9058 0.5879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6379 0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5889 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 2.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8979 -0.6722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 3.0879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 4 20 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 10 1 0 0 0 0 8 12 1 0 0 0 0 10 2 1 1 0 0 0 10 18 1 0 0 0 0 11 3 1 1 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 7 1 1 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	327.285
LogP:	5.703
LogD:	4.365
LogS:	-5.688
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	4.297
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:	-4.76
MDCK Permeability:	1.6655571016599424e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.27
Plasma Protein Binding (PPB):	98.49675750732422%
Volume Distribution (VD):	2.0
Pgp-substrate:	1.8497711420059204%

ADMET: Metabolism

CYP1A2-inhibitor:	0.551
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.405
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.601
CYP3A4-inhibitor:	0.404
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	4.802
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.778
Carcinogencity:	0.063
Eye Corrosion:	0.014
Eye Irritation:	0.362
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC151045

Natural Product ID:	NPC151045
*Common Name:**	Sikkimenoid A
IUPAC Name:	n.a.
Synonyms:	Sikkimenoid A
Standard InCHIKey:	VYBBQJWRIBGXEQ-BTVLNHBSSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-9-6-7-13-17(20(13,4)5)15-11(3)19(22)12-8-10(2)18(21)16(12)14(9)15/h10-11,13-15,17H,1,6-8H2,2-5H3/t10-,11-,13-,14+,15-,17-/m0/s1
SMILES:	C=C1CC[C@H]2[C@@H]([C@@H]3[C@@H]1C1=C(C[C@@H](C1=O)C)C(=O)[C@H]3C)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334877
PubChem CID:	71579129
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[561988]

☑ 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 NPC151045 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	279
0.1-0.2	3642
0.2-0.3	18011
0.3-0.4	11330
0.4-0.5	6767
0.5-0.6	2323
0.6-0.7	292
0.7-0.8	47
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	NPC246722
0.8382	Intermediate Similarity	NPC470329
0.8235	Intermediate Similarity	NPC285371
0.8235	Intermediate Similarity	NPC6697
0.8228	Intermediate Similarity	NPC15838
0.8228	Intermediate Similarity	NPC132629
0.8209	Intermediate Similarity	NPC213152
0.8194	Intermediate Similarity	NPC5701
0.8169	Intermediate Similarity	NPC256846
0.8143	Intermediate Similarity	NPC475523
0.8056	Intermediate Similarity	NPC307176
0.8	Intermediate Similarity	NPC69408
0.7973	Intermediate Similarity	NPC255021
0.7971	Intermediate Similarity	NPC473902
0.7971	Intermediate Similarity	NPC212210
0.7945	Intermediate Similarity	NPC223187
0.7941	Intermediate Similarity	NPC475795
0.7941	Intermediate Similarity	NPC97322
0.7917	Intermediate Similarity	NPC139397
0.7879	Intermediate Similarity	NPC192427
0.7857	Intermediate Similarity	NPC251118
0.7838	Intermediate Similarity	NPC303613
0.7838	Intermediate Similarity	NPC474228
0.7826	Intermediate Similarity	NPC165695
0.7826	Intermediate Similarity	NPC472306
0.7826	Intermediate Similarity	NPC32285
0.7808	Intermediate Similarity	NPC260040
0.7808	Intermediate Similarity	NPC35734
0.7808	Intermediate Similarity	NPC265782
0.7808	Intermediate Similarity	NPC2634
0.7808	Intermediate Similarity	NPC251929
0.7808	Intermediate Similarity	NPC159577
0.7808	Intermediate Similarity	NPC282593
0.7794	Intermediate Similarity	NPC127582
0.7778	Intermediate Similarity	NPC87141
0.7778	Intermediate Similarity	NPC260474
0.7778	Intermediate Similarity	NPC188292
0.7761	Intermediate Similarity	NPC27610
0.7761	Intermediate Similarity	NPC56905
0.7727	Intermediate Similarity	NPC20603
0.7714	Intermediate Similarity	NPC475124
0.7703	Intermediate Similarity	NPC54123
0.7703	Intermediate Similarity	NPC115023
0.7703	Intermediate Similarity	NPC474562
0.7703	Intermediate Similarity	NPC304983
0.7692	Intermediate Similarity	NPC90965
0.7681	Intermediate Similarity	NPC60565
0.7647	Intermediate Similarity	NPC259261
0.7647	Intermediate Similarity	NPC472304
0.7647	Intermediate Similarity	NPC276764
0.7632	Intermediate Similarity	NPC255650
0.7632	Intermediate Similarity	NPC473171
0.7612	Intermediate Similarity	NPC193695
0.76	Intermediate Similarity	NPC470044
0.76	Intermediate Similarity	NPC470045
0.76	Intermediate Similarity	NPC251705
0.7571	Intermediate Similarity	NPC288253
0.7568	Intermediate Similarity	NPC214770
0.7568	Intermediate Similarity	NPC477856
0.7538	Intermediate Similarity	NPC474141
0.7536	Intermediate Similarity	NPC25853
0.7534	Intermediate Similarity	NPC155198
0.7534	Intermediate Similarity	NPC310992
0.7534	Intermediate Similarity	NPC20610
0.75	Intermediate Similarity	NPC170799
0.75	Intermediate Similarity	NPC311852
0.75	Intermediate Similarity	NPC266295
0.75	Intermediate Similarity	NPC30215
0.75	Intermediate Similarity	NPC308108
0.75	Intermediate Similarity	NPC94991
0.75	Intermediate Similarity	NPC309852
0.7467	Intermediate Similarity	NPC305501
0.7467	Intermediate Similarity	NPC190035
0.7467	Intermediate Similarity	NPC234707
0.7465	Intermediate Similarity	NPC469662
0.7432	Intermediate Similarity	NPC61702
0.7432	Intermediate Similarity	NPC182815
0.7432	Intermediate Similarity	NPC477857
0.7432	Intermediate Similarity	NPC162867
0.7403	Intermediate Similarity	NPC293803
0.7368	Intermediate Similarity	NPC56747
0.7368	Intermediate Similarity	NPC474488
0.7368	Intermediate Similarity	NPC109576
0.7368	Intermediate Similarity	NPC130016
0.7368	Intermediate Similarity	NPC180015
0.7353	Intermediate Similarity	NPC115385
0.7353	Intermediate Similarity	NPC267626
0.7353	Intermediate Similarity	NPC49575
0.7353	Intermediate Similarity	NPC55004
0.7342	Intermediate Similarity	NPC469996
0.7342	Intermediate Similarity	NPC115515
0.7324	Intermediate Similarity	NPC202118
0.7324	Intermediate Similarity	NPC167256
0.7324	Intermediate Similarity	NPC197238
0.7317	Intermediate Similarity	NPC41539
0.7273	Intermediate Similarity	NPC268564
0.7273	Intermediate Similarity	NPC474797
0.7273	Intermediate Similarity	NPC474796
0.7273	Intermediate Similarity	NPC329866
0.726	Intermediate Similarity	NPC189917
0.726	Intermediate Similarity	NPC107704
0.726	Intermediate Similarity	NPC96812
0.726	Intermediate Similarity	NPC323005
0.726	Intermediate Similarity	NPC39462
0.726	Intermediate Similarity	NPC168824
0.725	Intermediate Similarity	NPC170793
0.7237	Intermediate Similarity	NPC181204
0.7237	Intermediate Similarity	NPC470078
0.7229	Intermediate Similarity	NPC320801
0.72	Intermediate Similarity	NPC286814
0.7195	Intermediate Similarity	NPC472867
0.7179	Intermediate Similarity	NPC65650
0.7179	Intermediate Similarity	NPC476346
0.7162	Intermediate Similarity	NPC4370
0.7162	Intermediate Similarity	NPC290350
0.716	Intermediate Similarity	NPC474509
0.7143	Intermediate Similarity	NPC143834
0.7143	Intermediate Similarity	NPC11711
0.7143	Intermediate Similarity	NPC8571
0.7143	Intermediate Similarity	NPC94531
0.7143	Intermediate Similarity	NPC142649
0.7143	Intermediate Similarity	NPC311702
0.7143	Intermediate Similarity	NPC472940
0.7143	Intermediate Similarity	NPC472931
0.7143	Intermediate Similarity	NPC123319
0.7125	Intermediate Similarity	NPC228911
0.7105	Intermediate Similarity	NPC40574
0.7101	Intermediate Similarity	NPC230823
0.7093	Intermediate Similarity	NPC474854
0.7089	Intermediate Similarity	NPC469796
0.7089	Intermediate Similarity	NPC469793
0.7089	Intermediate Similarity	NPC180886
0.7089	Intermediate Similarity	NPC1254
0.7077	Intermediate Similarity	NPC116906
0.7073	Intermediate Similarity	NPC477372
0.7073	Intermediate Similarity	NPC136150
0.7073	Intermediate Similarity	NPC189237
0.7067	Intermediate Similarity	NPC296697
0.7067	Intermediate Similarity	NPC142754
0.7067	Intermediate Similarity	NPC39157
0.7067	Intermediate Similarity	NPC82477
0.7059	Intermediate Similarity	NPC6247
0.7059	Intermediate Similarity	NPC200258
0.7042	Intermediate Similarity	NPC270042
0.7037	Intermediate Similarity	NPC472490
0.7027	Intermediate Similarity	NPC92327
0.7027	Intermediate Similarity	NPC176171
0.7024	Intermediate Similarity	NPC181743
0.7024	Intermediate Similarity	NPC16287
0.7024	Intermediate Similarity	NPC178025
0.7015	Intermediate Similarity	NPC296311
0.7015	Intermediate Similarity	NPC23117
0.7013	Intermediate Similarity	NPC133253
0.7013	Intermediate Similarity	NPC225467
0.7	Intermediate Similarity	NPC472300
0.6988	Remote Similarity	NPC477271
0.6988	Remote Similarity	NPC320514
0.6988	Remote Similarity	NPC142253
0.6988	Remote Similarity	NPC193347
0.6988	Remote Similarity	NPC321289
0.6988	Remote Similarity	NPC472239
0.6988	Remote Similarity	NPC477269
0.6988	Remote Similarity	NPC129080
0.6988	Remote Similarity	NPC477270
0.6988	Remote Similarity	NPC3511
0.6988	Remote Similarity	NPC327969
0.6986	Remote Similarity	NPC4638
0.697	Remote Similarity	NPC236623
0.697	Remote Similarity	NPC64866
0.6962	Remote Similarity	NPC469678
0.6962	Remote Similarity	NPC469669
0.6962	Remote Similarity	NPC475771
0.6957	Remote Similarity	NPC473733
0.6951	Remote Similarity	NPC26139
0.6951	Remote Similarity	NPC472478
0.6941	Remote Similarity	NPC179006
0.6941	Remote Similarity	NPC60350
0.6941	Remote Similarity	NPC474853
0.6933	Remote Similarity	NPC220210
0.6933	Remote Similarity	NPC20181
0.6933	Remote Similarity	NPC176107
0.6923	Remote Similarity	NPC52667
0.6914	Remote Similarity	NPC23778
0.6914	Remote Similarity	NPC189485
0.6914	Remote Similarity	NPC275494
0.6914	Remote Similarity	NPC470052
0.6914	Remote Similarity	NPC82635
0.6914	Remote Similarity	NPC471409
0.6914	Remote Similarity	NPC74410
0.6912	Remote Similarity	NPC5626
0.6905	Remote Similarity	NPC469561
0.6905	Remote Similarity	NPC470015
0.6905	Remote Similarity	NPC271784
0.6905	Remote Similarity	NPC470165
0.6905	Remote Similarity	NPC168188
0.6901	Remote Similarity	NPC285594
0.6901	Remote Similarity	NPC96551
0.6875	Remote Similarity	NPC473223
0.6842	Remote Similarity	NPC469679
0.6835	Remote Similarity	NPC219232

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 NPC151045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	3639
0.2-0.3	4015
0.3-0.4	833
0.4-0.5	300
0.5-0.6	98
0.6-0.7	12
0.7-0.8	0
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
0.8056	Intermediate Similarity	NPD4747	Approved
0.7917	Intermediate Similarity	NPD4137	Phase 3
0.7808	Intermediate Similarity	NPD4691	Approved
0.7733	Intermediate Similarity	NPD5733	Approved
0.7733	Intermediate Similarity	NPD4687	Approved
0.7703	Intermediate Similarity	NPD5276	Approved
0.75	Intermediate Similarity	NPD287	Approved
0.75	Intermediate Similarity	NPD4058	Approved
0.7297	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4221	Approved
0.6988	Remote Similarity	NPD4223	Phase 3
0.6824	Remote Similarity	NPD4197	Approved
0.6744	Remote Similarity	NPD5329	Approved
0.6707	Remote Similarity	NPD3617	Approved
0.6706	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6628	Remote Similarity	NPD3665	Phase 1
0.6628	Remote Similarity	NPD3666	Approved
0.6628	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD4695	Discontinued
0.6522	Remote Similarity	NPD6001	Approved
0.6517	Remote Similarity	NPD6672	Approved
0.6517	Remote Similarity	NPD5208	Approved
0.6517	Remote Similarity	NPD5737	Approved
0.6477	Remote Similarity	NPD7146	Approved
0.6477	Remote Similarity	NPD5279	Phase 3
0.6477	Remote Similarity	NPD3618	Phase 1
0.6477	Remote Similarity	NPD5330	Approved
0.6477	Remote Similarity	NPD6684	Approved
0.6477	Remote Similarity	NPD7521	Approved
0.6477	Remote Similarity	NPD7334	Approved
0.6477	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD8028	Phase 2
0.6452	Remote Similarity	NPD4629	Approved
0.6452	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5210	Approved
0.6444	Remote Similarity	NPD6904	Approved
0.6444	Remote Similarity	NPD6673	Approved
0.6444	Remote Similarity	NPD6080	Approved
0.6444	Remote Similarity	NPD4753	Phase 2
0.6444	Remote Similarity	NPD5328	Approved
0.6437	Remote Similarity	NPD4786	Approved
0.6413	Remote Similarity	NPD5133	Approved
0.6395	Remote Similarity	NPD3667	Approved
0.6374	Remote Similarity	NPD5692	Phase 3
0.6374	Remote Similarity	NPD5207	Approved
0.6364	Remote Similarity	NPD7331	Phase 2
0.6333	Remote Similarity	NPD6903	Approved
0.6333	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6050	Approved
0.6304	Remote Similarity	NPD5693	Phase 1
0.6304	Remote Similarity	NPD6079	Approved
0.6304	Remote Similarity	NPD5281	Approved
0.6304	Remote Similarity	NPD5694	Approved
0.6304	Remote Similarity	NPD5284	Approved
0.6292	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6098	Approved
0.6279	Remote Similarity	NPD4139	Approved
0.6279	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.6237	Remote Similarity	NPD4202	Approved
0.6235	Remote Similarity	NPD4195	Approved
0.6234	Remote Similarity	NPD7341	Phase 2
0.6222	Remote Similarity	NPD3573	Approved
0.6196	Remote Similarity	NPD4096	Approved
0.618	Remote Similarity	NPD1696	Phase 3
0.6154	Remote Similarity	NPD4518	Approved
0.6146	Remote Similarity	NPD5959	Approved
0.6105	Remote Similarity	NPD5695	Phase 3
0.6061	Remote Similarity	NPD5091	Approved
0.6042	Remote Similarity	NPD5221	Approved
0.6042	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4697	Phase 3
0.6042	Remote Similarity	NPD5222	Approved
0.6023	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4755	Approved
0.5979	Remote Similarity	NPD6083	Phase 2
0.5979	Remote Similarity	NPD6084	Phase 2
0.5979	Remote Similarity	NPD5173	Approved
0.5957	Remote Similarity	NPD7515	Phase 2
0.5955	Remote Similarity	NPD4788	Approved
0.5938	Remote Similarity	NPD5654	Approved
0.5914	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6399	Phase 3
0.589	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7732	Phase 3
0.5876	Remote Similarity	NPD7614	Phase 1
0.5859	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD5286	Approved
0.5859	Remote Similarity	NPD4696	Approved
0.5859	Remote Similarity	NPD4700	Approved
0.5844	Remote Similarity	NPD4194	Approved
0.5844	Remote Similarity	NPD4192	Approved
0.5844	Remote Similarity	NPD4191	Approved
0.5844	Remote Similarity	NPD4193	Approved
0.5843	Remote Similarity	NPD5209	Approved
0.5833	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7748	Approved
0.5833	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD6614	Approved
0.5824	Remote Similarity	NPD1694	Approved
0.58	Remote Similarity	NPD5223	Approved
0.5795	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4633	Approved
0.5743	Remote Similarity	NPD5224	Approved
0.5743	Remote Similarity	NPD5226	Approved
0.5743	Remote Similarity	NPD5211	Phase 2
0.5743	Remote Similarity	NPD5225	Approved
0.5728	Remote Similarity	NPD6008	Approved
0.5686	Remote Similarity	NPD5174	Approved
0.5686	Remote Similarity	NPD6052	Approved
0.5686	Remote Similarity	NPD5175	Approved
0.5686	Remote Similarity	NPD4754	Approved
0.5657	Remote Similarity	NPD3495	Discontinued
0.5657	Remote Similarity	NPD7902	Approved
0.5652	Remote Similarity	NPD344	Approved
0.5652	Remote Similarity	NPD343	Approved
0.5652	Remote Similarity	NPD345	Approved
0.5631	Remote Similarity	NPD5141	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