NPASS Compound

Structure

CID30502 OpenBabel06191715362D 25 27 0 0 1 0 0 0 0 0999 V2000 6.0006 -4.2961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6479 -3.7609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0298 -1.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 -3.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 -1.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3825 -2.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7134 -3.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0140 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4263 -0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6697 -3.5529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 -2.6019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7353 -2.9292 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4263 -1.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0933 1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 -1.4781 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 14 1 0 0 0 0 2 14 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 15 3 1 6 0 0 0 16 4 1 1 0 0 0 16 17 1 0 0 0 0 17 21 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 6 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 21 5 1 6 0 0 0 22 24 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	4.828
LogD:	4.428
LogS:	-5.541
# Rotatable Bonds:	5
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	4.841
Fsp3:	0.773
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:	-4.616
MDCK Permeability:	3.5096843930659816e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.352

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	84.69353485107422%
Volume Distribution (VD):	1.22
Pgp-substrate:	2.445434331893921%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.72
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.324
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	6.68
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.407
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.573
Skin Sensitization:	0.602
Carcinogencity:	0.034
Eye Corrosion:	0.05
Eye Irritation:	0.2
Respiratory Toxicity:	0.551

Download Data

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

Natural Product: NPC30502

Natural Product ID:	NPC30502
*Common Name:**	Volemolide
IUPAC Name:	(3aS,5aR,6R,8aR)-6-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3a-methoxy-5a-methyl-4,5,6,7,8,8a-hexahydrocyclopenta[e][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	FCFUSYHGZLEMJM-IIVOHCRVSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-14(2)15(3)7-8-16(4)17-9-10-18-19-13-20(23)25-22(19,24-6)12-11-21(17,18)5/h7-8,13-18H,9-12H2,1-6H3/b8-7+/t15-,16+,17+,18-,21+,22-/m0/s1
SMILES:	CO[C@@]12CC[C@]3([C@H](C2=CC(=O)O1)CC[C@@H]3[C@@H](/C=C/[C@@H](C(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593355
PubChem CID:	14584691
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10423860]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15863936]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21848266]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848266]
NPO33483	Diaporthe sp.	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23006147]
NPO33483	Diaporthe sp.	Species	Diaporthaceae	Eukaryota	n.a.	Mangrove-Derived Endophytic Fungus Diaporthe sp.	n.a.	PMID[23006147]
NPO33483	Diaporthe sp.	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26186257]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10.0	ug.mL-1	PMID[522887]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	10.0	ug.mL-1	PMID[522887]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10.0	ug.mL-1	PMID[522887]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	10.0	ug.mL-1	PMID[522887]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	10.0	ug.mL-1	PMID[522887]

☑ 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 NPC30502 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	175
0.1-0.2	1276
0.2-0.3	5646
0.3-0.4	15884
0.4-0.5	8534
0.5-0.6	7779
0.6-0.7	3014
0.7-0.8	377
0.8-0.85	7
0.85-0.9	0
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC473659
0.9259	High Similarity	NPC474694
0.9259	High Similarity	NPC475860
0.9136	High Similarity	NPC474693
0.8235	Intermediate Similarity	NPC96055
0.8171	Intermediate Similarity	NPC184737
0.814	Intermediate Similarity	NPC472442
0.8118	Intermediate Similarity	NPC472440
0.809	Intermediate Similarity	NPC302280
0.8049	Intermediate Similarity	NPC189206
0.8	Intermediate Similarity	NPC471218
0.7976	Intermediate Similarity	NPC10636
0.7976	Intermediate Similarity	NPC268827
0.7931	Intermediate Similarity	NPC474013
0.7826	Intermediate Similarity	NPC201725
0.7816	Intermediate Similarity	NPC475100
0.7802	Intermediate Similarity	NPC329842
0.7789	Intermediate Similarity	NPC472826
0.7778	Intermediate Similarity	NPC177141
0.7778	Intermediate Similarity	NPC476489
0.7778	Intermediate Similarity	NPC476490
0.7701	Intermediate Similarity	NPC12283
0.7701	Intermediate Similarity	NPC474193
0.7692	Intermediate Similarity	NPC273199
0.7667	Intermediate Similarity	NPC471956
0.7667	Intermediate Similarity	NPC93411
0.7667	Intermediate Similarity	NPC473879
0.7647	Intermediate Similarity	NPC170561
0.764	Intermediate Similarity	NPC131813
0.7634	Intermediate Similarity	NPC470255
0.7619	Intermediate Similarity	NPC54996
0.7614	Intermediate Similarity	NPC471301
0.7614	Intermediate Similarity	NPC471302
0.7609	Intermediate Similarity	NPC472811
0.7604	Intermediate Similarity	NPC201406
0.7595	Intermediate Similarity	NPC472266
0.7582	Intermediate Similarity	NPC288699
0.7582	Intermediate Similarity	NPC285982
0.7579	Intermediate Similarity	NPC231751
0.7579	Intermediate Similarity	NPC476768
0.7576	Intermediate Similarity	NPC127790
0.7558	Intermediate Similarity	NPC472470
0.7558	Intermediate Similarity	NPC469802
0.7529	Intermediate Similarity	NPC105197
0.7528	Intermediate Similarity	NPC471795
0.7528	Intermediate Similarity	NPC42586
0.7528	Intermediate Similarity	NPC473251
0.7527	Intermediate Similarity	NPC472812
0.7527	Intermediate Similarity	NPC472303
0.7526	Intermediate Similarity	NPC222875
0.7526	Intermediate Similarity	NPC295110
0.7526	Intermediate Similarity	NPC25177
0.7526	Intermediate Similarity	NPC268829
0.7526	Intermediate Similarity	NPC247701
0.7525	Intermediate Similarity	NPC475030
0.75	Intermediate Similarity	NPC78973
0.75	Intermediate Similarity	NPC476317
0.75	Intermediate Similarity	NPC310479
0.75	Intermediate Similarity	NPC182136
0.75	Intermediate Similarity	NPC477124
0.75	Intermediate Similarity	NPC311070
0.75	Intermediate Similarity	NPC321385
0.75	Intermediate Similarity	NPC474440
0.7475	Intermediate Similarity	NPC472819
0.7473	Intermediate Similarity	NPC472378
0.7473	Intermediate Similarity	NPC472810
0.7473	Intermediate Similarity	NPC472809
0.7471	Intermediate Similarity	NPC170303
0.747	Intermediate Similarity	NPC475517
0.747	Intermediate Similarity	NPC474524
0.7468	Intermediate Similarity	NPC116013
0.7447	Intermediate Similarity	NPC477722
0.7444	Intermediate Similarity	NPC471219
0.7442	Intermediate Similarity	NPC44083
0.7442	Intermediate Similarity	NPC153987
0.7442	Intermediate Similarity	NPC190211
0.7419	Intermediate Similarity	NPC177641
0.7419	Intermediate Similarity	NPC472953
0.7419	Intermediate Similarity	NPC289479
0.7416	Intermediate Similarity	NPC318515
0.7412	Intermediate Similarity	NPC476439
0.7407	Intermediate Similarity	NPC22301
0.7407	Intermediate Similarity	NPC265574
0.74	Intermediate Similarity	NPC85670
0.74	Intermediate Similarity	NPC239961
0.74	Intermediate Similarity	NPC472818
0.7396	Intermediate Similarity	NPC110937
0.7396	Intermediate Similarity	NPC476253
0.7391	Intermediate Similarity	NPC470734
0.7386	Intermediate Similarity	NPC256112
0.7386	Intermediate Similarity	NPC200513
0.7386	Intermediate Similarity	NPC471298
0.7374	Intermediate Similarity	NPC97487
0.7374	Intermediate Similarity	NPC120009
0.7374	Intermediate Similarity	NPC112009
0.7374	Intermediate Similarity	NPC160583
0.7374	Intermediate Similarity	NPC187302
0.7374	Intermediate Similarity	NPC189588
0.7374	Intermediate Similarity	NPC196471
0.7374	Intermediate Similarity	NPC180204
0.7374	Intermediate Similarity	NPC10232
0.7368	Intermediate Similarity	NPC472441
0.7368	Intermediate Similarity	NPC474909
0.7368	Intermediate Similarity	NPC471362
0.7368	Intermediate Similarity	NPC33473
0.7368	Intermediate Similarity	NPC471372
0.7368	Intermediate Similarity	NPC472189
0.7368	Intermediate Similarity	NPC281134
0.7363	Intermediate Similarity	NPC476600
0.7363	Intermediate Similarity	NPC471796
0.7363	Intermediate Similarity	NPC471657
0.7363	Intermediate Similarity	NPC45957
0.7356	Intermediate Similarity	NPC233332
0.7349	Intermediate Similarity	NPC222244
0.7349	Intermediate Similarity	NPC16349
0.7347	Intermediate Similarity	NPC198992
0.734	Intermediate Similarity	NPC38232
0.734	Intermediate Similarity	NPC162615
0.734	Intermediate Similarity	NPC205034
0.734	Intermediate Similarity	NPC53555
0.734	Intermediate Similarity	NPC152778
0.734	Intermediate Similarity	NPC7349
0.7333	Intermediate Similarity	NPC30984
0.7333	Intermediate Similarity	NPC189311
0.7327	Intermediate Similarity	NPC472820
0.7326	Intermediate Similarity	NPC471220
0.732	Intermediate Similarity	NPC252295
0.732	Intermediate Similarity	NPC473154
0.7317	Intermediate Similarity	NPC64234
0.7317	Intermediate Similarity	NPC37929
0.7312	Intermediate Similarity	NPC280149
0.7312	Intermediate Similarity	NPC221111
0.7303	Intermediate Similarity	NPC476927
0.7303	Intermediate Similarity	NPC139206
0.7303	Intermediate Similarity	NPC472473
0.7303	Intermediate Similarity	NPC471297
0.7303	Intermediate Similarity	NPC193198
0.7303	Intermediate Similarity	NPC474809
0.73	Intermediate Similarity	NPC189616
0.7292	Intermediate Similarity	NPC171598
0.7292	Intermediate Similarity	NPC307164
0.7292	Intermediate Similarity	NPC470801
0.7292	Intermediate Similarity	NPC16967
0.7283	Intermediate Similarity	NPC226863
0.7283	Intermediate Similarity	NPC106332
0.7273	Intermediate Similarity	NPC471993
0.7273	Intermediate Similarity	NPC25554
0.7273	Intermediate Similarity	NPC472471
0.7273	Intermediate Similarity	NPC476769
0.7263	Intermediate Similarity	NPC105490
0.7263	Intermediate Similarity	NPC120351
0.7263	Intermediate Similarity	NPC161998
0.7263	Intermediate Similarity	NPC471994
0.7263	Intermediate Similarity	NPC298973
0.7263	Intermediate Similarity	NPC104925
0.7263	Intermediate Similarity	NPC128488
0.7263	Intermediate Similarity	NPC166143
0.7263	Intermediate Similarity	NPC140277
0.7263	Intermediate Similarity	NPC469697
0.7263	Intermediate Similarity	NPC304968
0.7255	Intermediate Similarity	NPC61411
0.7253	Intermediate Similarity	NPC286153
0.7253	Intermediate Similarity	NPC118266
0.725	Intermediate Similarity	NPC185587
0.7245	Intermediate Similarity	NPC473219
0.7245	Intermediate Similarity	NPC324841
0.7245	Intermediate Similarity	NPC470761
0.7245	Intermediate Similarity	NPC470906
0.7241	Intermediate Similarity	NPC469690
0.7241	Intermediate Similarity	NPC242767
0.7234	Intermediate Similarity	NPC2882
0.7234	Intermediate Similarity	NPC477122
0.7234	Intermediate Similarity	NPC141831
0.7234	Intermediate Similarity	NPC234335
0.7229	Intermediate Similarity	NPC257618
0.7228	Intermediate Similarity	NPC186668
0.7228	Intermediate Similarity	NPC220217
0.7228	Intermediate Similarity	NPC119855
0.7222	Intermediate Similarity	NPC238197
0.7222	Intermediate Similarity	NPC71626
0.7222	Intermediate Similarity	NPC306951
0.7222	Intermediate Similarity	NPC149869
0.7222	Intermediate Similarity	NPC30486
0.7216	Intermediate Similarity	NPC472188
0.7216	Intermediate Similarity	NPC2049
0.7215	Intermediate Similarity	NPC329698
0.7209	Intermediate Similarity	NPC473756
0.7204	Intermediate Similarity	NPC251528
0.7204	Intermediate Similarity	NPC474396
0.7204	Intermediate Similarity	NPC262858
0.7204	Intermediate Similarity	NPC293044
0.7204	Intermediate Similarity	NPC472240
0.7204	Intermediate Similarity	NPC50488
0.72	Intermediate Similarity	NPC471365
0.72	Intermediate Similarity	NPC297617
0.72	Intermediate Similarity	NPC45897
0.72	Intermediate Similarity	NPC472821
0.72	Intermediate Similarity	NPC476770
0.72	Intermediate Similarity	NPC471364
0.72	Intermediate Similarity	NPC281378

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 NPC30502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1557
0.2-0.3	4323
0.3-0.4	2257
0.4-0.5	489
0.5-0.6	259
0.6-0.7	109
0.7-0.8	3
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
0.7386	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6051	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6903	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.6909	Remote Similarity	NPD7516	Approved
0.6882	Remote Similarity	NPD7521	Approved
0.6882	Remote Similarity	NPD7146	Approved
0.6882	Remote Similarity	NPD6684	Approved
0.6882	Remote Similarity	NPD7334	Approved
0.6882	Remote Similarity	NPD5330	Approved
0.6882	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.6848	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8294	Approved
0.6847	Remote Similarity	NPD8377	Approved
0.6837	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8033	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6782	Remote Similarity	NPD8039	Approved
0.6771	Remote Similarity	NPD5207	Approved
0.6737	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD4225	Approved
0.6604	Remote Similarity	NPD6686	Approved
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6001	Approved
0.6562	Remote Similarity	NPD5208	Approved
0.6552	Remote Similarity	NPD7507	Approved
0.6531	Remote Similarity	NPD5694	Approved
0.6531	Remote Similarity	NPD7637	Suspended
0.6531	Remote Similarity	NPD6050	Approved
0.6526	Remote Similarity	NPD6098	Approved
0.6514	Remote Similarity	NPD6882	Approved
0.6491	Remote Similarity	NPD7503	Approved
0.6484	Remote Similarity	NPD4195	Approved
0.6465	Remote Similarity	NPD6399	Phase 3
0.6458	Remote Similarity	NPD3573	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD7115	Discovery
0.6429	Remote Similarity	NPD5785	Approved
0.6429	Remote Similarity	NPD5692	Phase 3
0.6408	Remote Similarity	NPD6648	Approved
0.6387	Remote Similarity	NPD7319	Approved
0.6383	Remote Similarity	NPD5362	Discontinued
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD6079	Approved
0.6346	Remote Similarity	NPD5344	Discontinued
0.6337	Remote Similarity	NPD5695	Phase 3
0.6327	Remote Similarity	NPD5328	Approved
0.6296	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6292	Remote Similarity	NPD6924	Approved
0.6292	Remote Similarity	NPD6926	Approved
0.6262	Remote Similarity	NPD6008	Approved
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD7151	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD7152	Approved
0.6238	Remote Similarity	NPD7900	Approved
0.6238	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7748	Approved
0.6237	Remote Similarity	NPD7525	Registered
0.6222	Remote Similarity	NPD7339	Approved
0.6222	Remote Similarity	NPD6942	Approved
0.6211	Remote Similarity	NPD6695	Phase 3
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.62	Remote Similarity	NPD5281	Approved
0.62	Remote Similarity	NPD5284	Approved
0.6186	Remote Similarity	NPD3618	Phase 1
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.617	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD6933	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD4786	Approved
0.6146	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4193	Approved
0.6145	Remote Similarity	NPD4191	Approved
0.6145	Remote Similarity	NPD4194	Approved
0.6145	Remote Similarity	NPD4192	Approved
0.6136	Remote Similarity	NPD7143	Approved
0.6136	Remote Similarity	NPD7144	Approved
0.6129	Remote Similarity	NPD6929	Approved
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD6617	Approved
0.6126	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD4785	Approved
0.6111	Remote Similarity	NPD4784	Approved
0.6105	Remote Similarity	NPD4221	Approved
0.6105	Remote Similarity	NPD4223	Phase 3
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6082	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5329	Approved
0.6075	Remote Similarity	NPD6052	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6067	Remote Similarity	NPD4243	Approved
0.6064	Remote Similarity	NPD6931	Approved
0.6064	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6930	Phase 2
0.6064	Remote Similarity	NPD7514	Phase 3
0.6058	Remote Similarity	NPD7902	Approved
0.6055	Remote Similarity	NPD5701	Approved
0.605	Remote Similarity	NPD7492	Approved
0.604	Remote Similarity	NPD8035	Phase 2
0.604	Remote Similarity	NPD8034	Phase 2
0.604	Remote Similarity	NPD7515	Phase 2
0.6024	Remote Similarity	NPD1145	Discontinued
0.6023	Remote Similarity	NPD6922	Approved
0.6023	Remote Similarity	NPD6923	Approved
0.6022	Remote Similarity	NPD7145	Approved
0.6022	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5690	Phase 2
0.602	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5654	Approved
0.6019	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6902	Approved
0.5983	Remote Similarity	NPD6054	Approved
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4202	Approved
0.5979	Remote Similarity	NPD3133	Approved
0.5979	Remote Similarity	NPD4197	Approved
0.5979	Remote Similarity	NPD3666	Approved
0.5979	Remote Similarity	NPD3665	Phase 1
0.5978	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5221	Approved
0.5962	Remote Similarity	NPD5222	Approved
0.5962	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.596	Remote Similarity	NPD7524	Approved
0.596	Remote Similarity	NPD7750	Discontinued
0.5955	Remote Similarity	NPD4747	Approved
0.595	Remote Similarity	NPD7078	Approved
0.5943	Remote Similarity	NPD6404	Discontinued
0.5941	Remote Similarity	NPD7838	Discovery
0.5938	Remote Similarity	NPD3667	Approved
0.5934	Remote Similarity	NPD4687	Approved
0.5934	Remote Similarity	NPD5733	Approved
0.5929	Remote Similarity	NPD6053	Discontinued
0.5922	Remote Similarity	NPD5707	Approved
0.5918	Remote Similarity	NPD5363	Approved
0.5914	Remote Similarity	NPD6925	Approved
0.5914	Remote Similarity	NPD6932	Approved
0.5914	Remote Similarity	NPD5776	Phase 2
0.5913	Remote Similarity	NPD6868	Approved
0.5909	Remote Similarity	NPD6614	Approved
0.5909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6412	Phase 2
0.5905	Remote Similarity	NPD5173	Approved
0.5905	Remote Similarity	NPD5959	Approved
0.5902	Remote Similarity	NPD7736	Approved
0.5895	Remote Similarity	NPD4822	Approved
0.5895	Remote Similarity	NPD7332	Phase 2
0.5895	Remote Similarity	NPD4821	Approved
0.5895	Remote Similarity	NPD4820	Approved
0.5895	Remote Similarity	NPD7509	Discontinued
0.5895	Remote Similarity	NPD4819	Approved
0.5889	Remote Similarity	NPD5276	Approved
0.5882	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD6411	Approved
0.5876	Remote Similarity	NPD7154	Phase 3
0.587	Remote Similarity	NPD8264	Approved
0.5859	Remote Similarity	NPD4694	Approved
0.5859	Remote Similarity	NPD4693	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