NPASS Compound

Structure

NPC76660 OpenBabel07101718282D 28 30 0 0 1 0 0 0 0 0999 V2000 6.3928 -0.0337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5002 -0.6801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8370 3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6398 0.6243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6923 2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6934 0.3011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2371 2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2946 0.9705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9002 1.0288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5068 2.5457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2910 1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4769 1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9404 0.9590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3232 0.9463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1336 1.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9999 0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9940 0.6358 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 2.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0800 2.2634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3806 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 -0.7852 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 5 1 0 0 0 0 3 10 2 0 0 0 0 4 11 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 2 1 1 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 7 1 1 0 0 0 12 16 1 0 0 0 0 13 8 1 6 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 1 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 11 1 1 0 0 0 16 19 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.22
Volume:	399.295
LogP:	-0.05
LogD:	0.859
LogS:	-2.171
# Rotatable Bonds:	6
TPSA:	116.09
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	5.034
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.996
MDCK Permeability:	5.552282527787611e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.126
Human Intestinal Absorption (HIA):	0.506
20% Bioavailability (F20%):	0.472
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	44.98796081542969%
Volume Distribution (VD):	0.427
Pgp-substrate:	59.30442810058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.521
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	4.236
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.58
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.621
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.044
Carcinogencity:	0.155
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC76660

Natural Product ID:	NPC76660
*Common Name:**	Pulchellamine G
IUPAC Name:	(2S,3R)-2-[[(3R,3aR,4S,6aR,8S,9aR,9bR)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-yl]methylamino]-3-methylpentanoic acid
Synonyms:	Pulchellamine G
Standard InCHIKey:	MMHJUQBMHBENCR-BRTRCFASSA-N
Standard InCHI:	InChI=1S/C21H31NO6/c1-5-9(2)18(20(25)26)22-8-13-17-15(24)6-10(3)12-7-14(23)11(4)16(12)19(17)28-21(13)27/h9,12-19,22-24H,3-8H2,1-2H3,(H,25,26)/t9-,12+,13+,14+,15+,16+,17-,18+,19-/m1/s1
SMILES:	CC[C@@H](C)[C@@H](C(=O)O)NC[C@H]1[C@@H]2[C@H](CC(=C)[C@@H]3C[C@@H](C(=C)[C@@H]3[C@H]2OC1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517193
PubChem CID:	24862585
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[18314958]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	uM	PMID[544917]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	uM	PMID[544917]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	uM	PMID[544917]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	uM	PMID[544917]

☑ 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 NPC76660 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	100
0.1-0.2	937
0.2-0.3	9035
0.3-0.4	18244
0.4-0.5	11308
0.5-0.6	2808
0.6-0.7	225
0.7-0.8	33
0.8-0.85	1
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC276995
0.9444	High Similarity	NPC209734
0.9231	High Similarity	NPC236644
0.8899	High Similarity	NPC469466
0.8704	High Similarity	NPC15413
0.8167	Intermediate Similarity	NPC474371
0.8	Intermediate Similarity	NPC265094
0.7727	Intermediate Similarity	NPC57976
0.7476	Intermediate Similarity	NPC128246
0.729	Intermediate Similarity	NPC217983
0.729	Intermediate Similarity	NPC207114
0.7282	Intermediate Similarity	NPC126248
0.7156	Intermediate Similarity	NPC19087
0.7143	Intermediate Similarity	NPC111409
0.7103	Intermediate Similarity	NPC187661
0.7097	Intermediate Similarity	NPC35037
0.7091	Intermediate Similarity	NPC475925
0.7091	Intermediate Similarity	NPC184063
0.7064	Intermediate Similarity	NPC38392
0.7034	Intermediate Similarity	NPC271562
0.7027	Intermediate Similarity	NPC475788
0.7	Intermediate Similarity	NPC297474
0.7	Intermediate Similarity	NPC54065
0.6972	Remote Similarity	NPC203170
0.6937	Remote Similarity	NPC171360
0.6937	Remote Similarity	NPC63193
0.6937	Remote Similarity	NPC29821
0.6937	Remote Similarity	NPC133888
0.6937	Remote Similarity	NPC57304
0.6937	Remote Similarity	NPC35959
0.6937	Remote Similarity	NPC293001
0.6916	Remote Similarity	NPC224386
0.6916	Remote Similarity	NPC194859
0.6909	Remote Similarity	NPC155935
0.6909	Remote Similarity	NPC215556
0.6847	Remote Similarity	NPC216284
0.6847	Remote Similarity	NPC35809
0.6842	Remote Similarity	NPC474297
0.6818	Remote Similarity	NPC79549
0.6783	Remote Similarity	NPC474313
0.6754	Remote Similarity	NPC472873
0.6754	Remote Similarity	NPC476053
0.6729	Remote Similarity	NPC246076
0.6726	Remote Similarity	NPC258216
0.6698	Remote Similarity	NPC258965
0.6698	Remote Similarity	NPC51507
0.6698	Remote Similarity	NPC156658
0.6696	Remote Similarity	NPC142529
0.6696	Remote Similarity	NPC91771
0.6696	Remote Similarity	NPC18019
0.6696	Remote Similarity	NPC24956
0.6694	Remote Similarity	NPC70235
0.6667	Remote Similarity	NPC198853
0.6638	Remote Similarity	NPC304445
0.6638	Remote Similarity	NPC236580
0.6638	Remote Similarity	NPC476344
0.6638	Remote Similarity	NPC471150
0.6637	Remote Similarity	NPC155215
0.6636	Remote Similarity	NPC56593
0.6636	Remote Similarity	NPC304558
0.661	Remote Similarity	NPC67296
0.6609	Remote Similarity	NPC170120
0.6609	Remote Similarity	NPC163228
0.6609	Remote Similarity	NPC213698
0.6609	Remote Similarity	NPC150041
0.6591	Remote Similarity	NPC476951
0.6589	Remote Similarity	NPC23963
0.6577	Remote Similarity	NPC118601
0.6577	Remote Similarity	NPC24728
0.6567	Remote Similarity	NPC478139
0.6545	Remote Similarity	NPC204105
0.6545	Remote Similarity	NPC90476
0.6545	Remote Similarity	NPC300082
0.6545	Remote Similarity	NPC69374
0.6545	Remote Similarity	NPC284534
0.6529	Remote Similarity	NPC195841
0.6529	Remote Similarity	NPC233256
0.6522	Remote Similarity	NPC127019
0.6522	Remote Similarity	NPC323008
0.6522	Remote Similarity	NPC470010
0.6522	Remote Similarity	NPC262133
0.6522	Remote Similarity	NPC470013
0.6522	Remote Similarity	NPC473331
0.6518	Remote Similarity	NPC178875
0.6518	Remote Similarity	NPC471149
0.6496	Remote Similarity	NPC58267
0.6496	Remote Similarity	NPC161493
0.6496	Remote Similarity	NPC263674
0.6496	Remote Similarity	NPC311904
0.6496	Remote Similarity	NPC261372
0.6491	Remote Similarity	NPC133698
0.6491	Remote Similarity	NPC131209
0.6486	Remote Similarity	NPC309757
0.6486	Remote Similarity	NPC64153
0.6486	Remote Similarity	NPC236692
0.6484	Remote Similarity	NPC235625
0.6484	Remote Similarity	NPC476952
0.6471	Remote Similarity	NPC171759
0.6471	Remote Similarity	NPC150923
0.6466	Remote Similarity	NPC317654
0.6466	Remote Similarity	NPC52044
0.6466	Remote Similarity	NPC304886
0.6466	Remote Similarity	NPC96010
0.6466	Remote Similarity	NPC67584
0.646	Remote Similarity	NPC472872
0.646	Remote Similarity	NPC283409
0.6441	Remote Similarity	NPC49833
0.6441	Remote Similarity	NPC249171
0.6435	Remote Similarity	NPC473263
0.6435	Remote Similarity	NPC308656
0.6435	Remote Similarity	NPC200237
0.6435	Remote Similarity	NPC60386
0.6435	Remote Similarity	NPC473273
0.6435	Remote Similarity	NPC473234
0.6417	Remote Similarity	NPC80144
0.641	Remote Similarity	NPC213078
0.6393	Remote Similarity	NPC471844
0.6391	Remote Similarity	NPC309525
0.6387	Remote Similarity	NPC471381
0.6387	Remote Similarity	NPC186861
0.6385	Remote Similarity	NPC230849
0.6379	Remote Similarity	NPC477131
0.637	Remote Similarity	NPC470539
0.6364	Remote Similarity	NPC473148
0.6364	Remote Similarity	NPC245665
0.6364	Remote Similarity	NPC215988
0.6357	Remote Similarity	NPC106791
0.6357	Remote Similarity	NPC201889
0.6356	Remote Similarity	NPC181151
0.6348	Remote Similarity	NPC191339
0.6348	Remote Similarity	NPC286341
0.6339	Remote Similarity	NPC470242
0.6325	Remote Similarity	NPC40663
0.6316	Remote Similarity	NPC12872
0.6316	Remote Similarity	NPC168679
0.6303	Remote Similarity	NPC45125
0.6303	Remote Similarity	NPC221615
0.6299	Remote Similarity	NPC130124
0.6299	Remote Similarity	NPC193471
0.6296	Remote Similarity	NPC478136
0.6293	Remote Similarity	NPC153590
0.6281	Remote Similarity	NPC86077
0.6277	Remote Similarity	NPC189393
0.6277	Remote Similarity	NPC90814
0.6271	Remote Similarity	NPC471843
0.627	Remote Similarity	NPC316984
0.627	Remote Similarity	NPC30911
0.626	Remote Similarity	NPC471259
0.626	Remote Similarity	NPC11379
0.626	Remote Similarity	NPC44004
0.626	Remote Similarity	NPC54737
0.626	Remote Similarity	NPC88190
0.625	Remote Similarity	NPC128698
0.625	Remote Similarity	NPC239768
0.6232	Remote Similarity	NPC133089
0.6228	Remote Similarity	NPC91248
0.6218	Remote Similarity	NPC170143
0.6218	Remote Similarity	NPC108475
0.6218	Remote Similarity	NPC213947
0.6216	Remote Similarity	NPC320936
0.6214	Remote Similarity	NPC5714
0.6214	Remote Similarity	NPC243902
0.6212	Remote Similarity	NPC476504
0.6198	Remote Similarity	NPC188785
0.6195	Remote Similarity	NPC162071
0.6195	Remote Similarity	NPC67493
0.6186	Remote Similarity	NPC167893
0.6183	Remote Similarity	NPC471261
0.6182	Remote Similarity	NPC470241
0.6179	Remote Similarity	NPC64168
0.6161	Remote Similarity	NPC165287
0.616	Remote Similarity	NPC68248
0.6159	Remote Similarity	NPC120335
0.6154	Remote Similarity	NPC472874
0.6154	Remote Similarity	NPC469998
0.6154	Remote Similarity	NPC65045
0.6154	Remote Similarity	NPC135776
0.6148	Remote Similarity	NPC471258
0.6148	Remote Similarity	NPC471263
0.6142	Remote Similarity	NPC168758
0.6142	Remote Similarity	NPC79238
0.6142	Remote Similarity	NPC181510
0.6142	Remote Similarity	NPC47857
0.614	Remote Similarity	NPC270270
0.614	Remote Similarity	NPC186148
0.614	Remote Similarity	NPC190753
0.614	Remote Similarity	NPC201658
0.614	Remote Similarity	NPC237540
0.614	Remote Similarity	NPC316629
0.614	Remote Similarity	NPC475773
0.6134	Remote Similarity	NPC160066
0.6134	Remote Similarity	NPC476009
0.6134	Remote Similarity	NPC126156
0.6129	Remote Similarity	NPC166115
0.6129	Remote Similarity	NPC243998
0.6126	Remote Similarity	NPC89555
0.6121	Remote Similarity	NPC37607
0.6121	Remote Similarity	NPC206614
0.6121	Remote Similarity	NPC301969
0.6121	Remote Similarity	NPC474323

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 NPC76660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	79
0.1-0.2	806
0.2-0.3	3694
0.3-0.4	3346
0.4-0.5	998
0.5-0.6	213
0.6-0.7	14
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
0.6336	Remote Similarity	NPD8269	Approved
0.6336	Remote Similarity	NPD8268	Approved
0.6336	Remote Similarity	NPD8266	Approved
0.6336	Remote Similarity	NPD8267	Approved
0.632	Remote Similarity	NPD6420	Discontinued
0.627	Remote Similarity	NPD2204	Approved
0.6204	Remote Similarity	NPD617	Approved
0.6195	Remote Similarity	NPD4249	Approved
0.6172	Remote Similarity	NPD1376	Discontinued
0.6154	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8273	Phase 1
0.614	Remote Similarity	NPD4250	Approved
0.614	Remote Similarity	NPD4251	Approved
0.6107	Remote Similarity	NPD7641	Discontinued
0.6074	Remote Similarity	NPD8340	Approved
0.6074	Remote Similarity	NPD8299	Approved
0.6074	Remote Similarity	NPD8342	Approved
0.6074	Remote Similarity	NPD8341	Approved
0.6063	Remote Similarity	NPD6421	Discontinued
0.6063	Remote Similarity	NPD8087	Discontinued
0.6061	Remote Similarity	NPD7519	Approved
0.6061	Remote Similarity	NPD7518	Approved
0.6061	Remote Similarity	NPD7517	Approved
0.6034	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD2613	Approved
0.5986	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD7751	Phase 1
0.597	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5362	Discontinued
0.5929	Remote Similarity	NPD2101	Approved
0.5912	Remote Similarity	NPD8451	Approved
0.5896	Remote Similarity	NPD8347	Approved
0.5896	Remote Similarity	NPD7147	Phase 3
0.5896	Remote Similarity	NPD8345	Approved
0.5896	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD8346	Approved
0.5882	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD2573	Approved
0.5874	Remote Similarity	NPD2571	Approved
0.5874	Remote Similarity	NPD3087	Approved
0.5874	Remote Similarity	NPD2566	Approved
0.5874	Remote Similarity	NPD2570	Approved
0.5874	Remote Similarity	NPD4745	Approved
0.5874	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD2574	Discontinued
0.5874	Remote Similarity	NPD3089	Approved
0.5874	Remote Similarity	NPD3616	Approved
0.5874	Remote Similarity	NPD3615	Approved
0.5874	Remote Similarity	NPD3088	Approved
0.5874	Remote Similarity	NPD4746	Phase 3
0.5874	Remote Similarity	NPD3090	Approved
0.5874	Remote Similarity	NPD3614	Approved
0.587	Remote Similarity	NPD8448	Approved
0.5868	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD8392	Approved
0.5857	Remote Similarity	NPD8390	Approved
0.5857	Remote Similarity	NPD8391	Approved
0.5852	Remote Similarity	NPD8444	Approved
0.5852	Remote Similarity	NPD6909	Approved
0.5852	Remote Similarity	NPD6908	Approved
0.5827	Remote Similarity	NPD8140	Approved
0.5827	Remote Similarity	NPD8337	Approved
0.5827	Remote Similarity	NPD8336	Approved
0.582	Remote Similarity	NPD3713	Approved
0.582	Remote Similarity	NPD3715	Approved
0.582	Remote Similarity	NPD3714	Approved
0.5809	Remote Similarity	NPD8080	Discontinued
0.5804	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD8415	Approved
0.5797	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD4685	Phase 3
0.5793	Remote Similarity	NPD4684	Phase 3
0.5793	Remote Similarity	NPD4686	Approved
0.5789	Remote Similarity	NPD7154	Phase 3
0.5785	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD1689	Approved
0.5775	Remote Similarity	NPD8449	Approved
0.5766	Remote Similarity	NPD7829	Approved
0.5766	Remote Similarity	NPD7642	Approved
0.5766	Remote Similarity	NPD7830	Approved
0.576	Remote Similarity	NPD8084	Approved
0.576	Remote Similarity	NPD8139	Approved
0.576	Remote Similarity	NPD8138	Approved
0.576	Remote Similarity	NPD8086	Approved
0.576	Remote Similarity	NPD8085	Approved
0.576	Remote Similarity	NPD8082	Approved
0.576	Remote Similarity	NPD8083	Approved
0.5748	Remote Similarity	NPD7333	Discontinued
0.5735	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5734	Remote Similarity	NPD8450	Suspended
0.5714	Remote Similarity	NPD8276	Approved
0.5714	Remote Similarity	NPD8275	Approved
0.5704	Remote Similarity	NPD3159	Discontinued
0.5703	Remote Similarity	NPD8307	Discontinued
0.5702	Remote Similarity	NPD7345	Approved
0.5702	Remote Similarity	NPD883	Phase 2
0.5702	Remote Similarity	NPD882	Phase 2
0.5702	Remote Similarity	NPD4270	Approved
0.5702	Remote Similarity	NPD6435	Approved
0.5702	Remote Similarity	NPD4269	Approved
0.5693	Remote Similarity	NPD7623	Phase 3
0.5693	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6371	Approved
0.5673	Remote Similarity	NPD9201	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8081	Approved
0.5664	Remote Similarity	NPD8338	Approved
0.5664	Remote Similarity	NPD4820	Approved
0.5664	Remote Similarity	NPD4822	Approved
0.5664	Remote Similarity	NPD4821	Approved
0.5664	Remote Similarity	NPD4819	Approved
0.5664	Remote Similarity	NPD6845	Suspended
0.5652	Remote Similarity	NPD7122	Discontinued
0.5641	Remote Similarity	NPD5786	Approved
0.563	Remote Similarity	NPD1773	Discontinued
0.5625	Remote Similarity	NPD8393	Approved
0.5625	Remote Similarity	NPD3732	Approved
0.5625	Remote Similarity	NPD4271	Approved
0.5625	Remote Similarity	NPD4268	Approved
0.5614	Remote Similarity	NPD857	Phase 3
0.5614	Remote Similarity	NPD5369	Approved
0.561	Remote Similarity	NPD7839	Suspended
0.5608	Remote Similarity	NPD6852	Discontinued
0.5606	Remote Similarity	NPD6429	Approved
0.5606	Remote Similarity	NPD6430	Approved
0.5606	Remote Similarity	NPD6053	Discontinued

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