NPASS Compound

Structure

NPC471816 OpenBabel07101718192D 30 32 0 0 1 0 0 0 0 0999 V2000 -0.8398 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4890 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0042 0.3549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8936 1.2647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 -1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4386 -2.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5020 -1.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9726 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3591 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1243 -1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8366 -0.0406 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8398 1.4545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 0.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0820 -1.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -0.4848 0.0000 C 0 0 2 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 4.1989 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 2.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5223 -2.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7693 0.5903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9883 0.9171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5223 -0.7263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 6 0 0 0 14 24 2 0 0 0 0 14 29 1 0 0 0 0 15 20 1 0 0 0 0 16 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 29 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 1 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 22 23 1 6 0 0 0 23 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.25
Volume:	434.317
LogP:	3.479
LogD:	3.108
LogS:	-4.215
# Rotatable Bonds:	6
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	4.94
Fsp3:	0.783
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.951
MDCK Permeability:	1.7946220395970158e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.496

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	88.89151763916016%
Volume Distribution (VD):	1.434
Pgp-substrate:	12.092792510986328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.413
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.11
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.342
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	6.945
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.697
Drug-inuced Liver Injury (DILI):	0.224
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.64
Maximum Recommended Daily Dose:	0.07
Skin Sensitization:	0.158
Carcinogencity:	0.123
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC471816

Natural Product ID:	NPC471816
*Common Name:**	(5S,6S,7R,8R,9R,10S)-6Beta-Acetoxy-7Beta,9Alpha-Dihydroxy-15-Methoxy-13(14)-Labden-16,15-Olide
IUPAC Name:	[(1S,2R,3R,4R,4aS,8aS)-2,4-dihydroxy-4-[2-(2-methoxy-5-oxo-2H-furan-4-yl)ethyl]-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	NXRPMVSGYGPUIP-SJODAWQKSA-N
Standard InCHI:	InChI=1S/C23H36O7/c1-13-17(25)18(29-14(2)24)19-21(3,4)9-7-10-22(19,5)23(13,27)11-8-15-12-16(28-6)30-20(15)26/h12-13,16-19,25,27H,7-11H2,1-6H3/t13-,16?,17-,18-,19+,22+,23-/m1/s1
SMILES:	CC1C(C(C2C(CCCC2(C1(CCC3=CC(OC3=O)OC)O)C)(C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234603
PubChem CID:	86302556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO17287	Lagopsis supina	Species	Lamiaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16200.0	nM	PMID[514880]

☑ 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 NPC471816 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	239
0.1-0.2	1440
0.2-0.3	4119
0.3-0.4	6488
0.4-0.5	11975
0.5-0.6	8977
0.6-0.7	6022
0.7-0.8	3175
0.8-0.85	222
0.85-0.9	36
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8868	High Similarity	NPC162973
0.885	High Similarity	NPC13713
0.885	High Similarity	NPC474483
0.8807	High Similarity	NPC392
0.8807	High Similarity	NPC177524
0.8807	High Similarity	NPC219900
0.8803	High Similarity	NPC469379
0.8803	High Similarity	NPC75856
0.8803	High Similarity	NPC86346
0.8774	High Similarity	NPC471412
0.8727	High Similarity	NPC206618
0.8718	High Similarity	NPC469382
0.8718	High Similarity	NPC27363
0.8716	High Similarity	NPC67321
0.8716	High Similarity	NPC187435
0.8684	High Similarity	NPC473968
0.8679	High Similarity	NPC471413
0.8655	High Similarity	NPC117702
0.8655	High Similarity	NPC146456
0.8655	High Similarity	NPC471356
0.8655	High Similarity	NPC179412
0.8655	High Similarity	NPC471357
0.8655	High Similarity	NPC469757
0.8636	High Similarity	NPC38948
0.8624	High Similarity	NPC51719
0.8621	High Similarity	NPC476150
0.8621	High Similarity	NPC476127
0.8621	High Similarity	NPC48692
0.8621	High Similarity	NPC470312
0.8584	High Similarity	NPC157441
0.8584	High Similarity	NPC311592
0.8584	High Similarity	NPC75167
0.8583	High Similarity	NPC270109
0.8571	High Similarity	NPC250556
0.8571	High Similarity	NPC469750
0.8545	High Similarity	NPC122816
0.8545	High Similarity	NPC471205
0.8534	High Similarity	NPC122971
0.8534	High Similarity	NPC475775
0.8534	High Similarity	NPC476529
0.8525	High Similarity	NPC93416
0.8519	High Similarity	NPC476081
0.8512	High Similarity	NPC471361
0.8512	High Similarity	NPC471360
0.8512	High Similarity	NPC469753
0.8512	High Similarity	NPC17896
0.8512	High Similarity	NPC197707
0.8512	High Similarity	NPC469752
0.8512	High Similarity	NPC469751
0.8512	High Similarity	NPC471359
0.8512	High Similarity	NPC10823
0.8512	High Similarity	NPC284406
0.8512	High Similarity	NPC251866
0.8512	High Similarity	NPC86159
0.8512	High Similarity	NPC70542
0.8512	High Similarity	NPC180079
0.8512	High Similarity	NPC219085
0.8512	High Similarity	NPC471358
0.8512	High Similarity	NPC471352
0.8512	High Similarity	NPC469754
0.8512	High Similarity	NPC469755
0.8512	High Similarity	NPC89514
0.8512	High Similarity	NPC9499
0.8512	High Similarity	NPC6108
0.8509	High Similarity	NPC181145
0.8505	High Similarity	NPC324841
0.85	High Similarity	NPC329784
0.85	High Similarity	NPC470780
0.85	High Similarity	NPC240070
0.8496	Intermediate Similarity	NPC222834
0.8496	Intermediate Similarity	NPC194951
0.8496	Intermediate Similarity	NPC12046
0.8482	Intermediate Similarity	NPC177047
0.8468	Intermediate Similarity	NPC181994
0.8468	Intermediate Similarity	NPC306265
0.8462	Intermediate Similarity	NPC151616
0.8462	Intermediate Similarity	NPC109607
0.8462	Intermediate Similarity	NPC107338
0.8443	Intermediate Similarity	NPC16569
0.8443	Intermediate Similarity	NPC253456
0.8443	Intermediate Similarity	NPC159338
0.844	Intermediate Similarity	NPC281378
0.844	Intermediate Similarity	NPC120009
0.8435	Intermediate Similarity	NPC138372
0.8435	Intermediate Similarity	NPC106228
0.843	Intermediate Similarity	NPC311534
0.843	Intermediate Similarity	NPC476859
0.8417	Intermediate Similarity	NPC222307
0.8407	Intermediate Similarity	NPC469655
0.8407	Intermediate Similarity	NPC469656
0.8407	Intermediate Similarity	NPC474846
0.8403	Intermediate Similarity	NPC473979
0.8396	Intermediate Similarity	NPC29952
0.8393	Intermediate Similarity	NPC299590
0.8393	Intermediate Similarity	NPC476759
0.839	Intermediate Similarity	NPC170084
0.839	Intermediate Similarity	NPC476204
0.8376	Intermediate Similarity	NPC469380
0.8374	Intermediate Similarity	NPC42670
0.8374	Intermediate Similarity	NPC19124
0.8374	Intermediate Similarity	NPC471855
0.8362	Intermediate Similarity	NPC23046
0.8361	Intermediate Similarity	NPC140092
0.8361	Intermediate Similarity	NPC276838
0.8361	Intermediate Similarity	NPC175186
0.8361	Intermediate Similarity	NPC232785
0.8361	Intermediate Similarity	NPC125077
0.8361	Intermediate Similarity	NPC329986
0.8361	Intermediate Similarity	NPC104382
0.8361	Intermediate Similarity	NPC91
0.8361	Intermediate Similarity	NPC188234
0.8349	Intermediate Similarity	NPC472815
0.8349	Intermediate Similarity	NPC472552
0.8349	Intermediate Similarity	NPC476769
0.8349	Intermediate Similarity	NPC295791
0.8349	Intermediate Similarity	NPC121423
0.8348	Intermediate Similarity	NPC472274
0.8347	Intermediate Similarity	NPC298841
0.8347	Intermediate Similarity	NPC42399
0.8333	Intermediate Similarity	NPC174836
0.8333	Intermediate Similarity	NPC470922
0.8333	Intermediate Similarity	NPC470063
0.8333	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC38855
0.8333	Intermediate Similarity	NPC472002
0.8319	Intermediate Similarity	NPC235014
0.8319	Intermediate Similarity	NPC83005
0.8319	Intermediate Similarity	NPC474567
0.8319	Intermediate Similarity	NPC119550
0.8306	Intermediate Similarity	NPC104585
0.8306	Intermediate Similarity	NPC88668
0.8306	Intermediate Similarity	NPC116075
0.8306	Intermediate Similarity	NPC298783
0.8306	Intermediate Similarity	NPC146857
0.8306	Intermediate Similarity	NPC157817
0.8306	Intermediate Similarity	NPC247190
0.8306	Intermediate Similarity	NPC32793
0.8306	Intermediate Similarity	NPC477709
0.8306	Intermediate Similarity	NPC476221
0.8306	Intermediate Similarity	NPC225385
0.8306	Intermediate Similarity	NPC469749
0.8305	Intermediate Similarity	NPC472004
0.8304	Intermediate Similarity	NPC217921
0.8304	Intermediate Similarity	NPC48548
0.8304	Intermediate Similarity	NPC128795
0.8304	Intermediate Similarity	NPC94942
0.8304	Intermediate Similarity	NPC135015
0.8293	Intermediate Similarity	NPC476855
0.8293	Intermediate Similarity	NPC476852
0.8293	Intermediate Similarity	NPC471170
0.8291	Intermediate Similarity	NPC124676
0.8291	Intermediate Similarity	NPC473828
0.8291	Intermediate Similarity	NPC146280
0.8291	Intermediate Similarity	NPC83287
0.8291	Intermediate Similarity	NPC473617
0.8288	Intermediate Similarity	NPC34768
0.8288	Intermediate Similarity	NPC239961
0.8288	Intermediate Similarity	NPC127609
0.8288	Intermediate Similarity	NPC218158
0.8276	Intermediate Similarity	NPC471127
0.8276	Intermediate Similarity	NPC234858
0.8276	Intermediate Similarity	NPC154363
0.8273	Intermediate Similarity	NPC61442
0.8273	Intermediate Similarity	NPC120321
0.8261	Intermediate Similarity	NPC264153
0.8257	Intermediate Similarity	NPC472554
0.8257	Intermediate Similarity	NPC198992
0.8257	Intermediate Similarity	NPC11974
0.8254	Intermediate Similarity	NPC59288
0.8254	Intermediate Similarity	NPC190065
0.8254	Intermediate Similarity	NPC141215
0.8254	Intermediate Similarity	NPC471089
0.824	Intermediate Similarity	NPC329636
0.8235	Intermediate Similarity	NPC202051
0.823	Intermediate Similarity	NPC472534
0.823	Intermediate Similarity	NPC316974
0.823	Intermediate Similarity	NPC40728
0.823	Intermediate Similarity	NPC143706
0.823	Intermediate Similarity	NPC112457
0.8226	Intermediate Similarity	NPC478154
0.8224	Intermediate Similarity	NPC134072
0.8224	Intermediate Similarity	NPC234993
0.822	Intermediate Similarity	NPC77689
0.822	Intermediate Similarity	NPC211093
0.822	Intermediate Similarity	NPC9674
0.822	Intermediate Similarity	NPC19028
0.822	Intermediate Similarity	NPC473636
0.822	Intermediate Similarity	NPC473839
0.8214	Intermediate Similarity	NPC125423
0.8214	Intermediate Similarity	NPC475074
0.8214	Intermediate Similarity	NPC88013
0.8211	Intermediate Similarity	NPC470851
0.8211	Intermediate Similarity	NPC477196
0.8211	Intermediate Similarity	NPC476854
0.8211	Intermediate Similarity	NPC476851
0.8211	Intermediate Similarity	NPC231529
0.8211	Intermediate Similarity	NPC471407
0.8211	Intermediate Similarity	NPC476966
0.8208	Intermediate Similarity	NPC105490
0.8205	Intermediate Similarity	NPC157376

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 NPC471816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1732
0.2-0.3	3626
0.3-0.4	2219
0.4-0.5	816
0.5-0.6	316
0.6-0.7	165
0.7-0.8	67
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD6686	Approved
0.8571	High Similarity	NPD7507	Approved
0.8512	High Similarity	NPD7319	Approved
0.8393	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8376	Intermediate Similarity	NPD7516	Approved
0.8291	Intermediate Similarity	NPD7328	Approved
0.8291	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD8378	Approved
0.7934	Intermediate Similarity	NPD8335	Approved
0.7934	Intermediate Similarity	NPD8380	Approved
0.7934	Intermediate Similarity	NPD8379	Approved
0.7934	Intermediate Similarity	NPD8296	Approved
0.7851	Intermediate Similarity	NPD8294	Approved
0.7851	Intermediate Similarity	NPD8377	Approved
0.7826	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD8033	Approved
0.7748	Intermediate Similarity	NPD7638	Approved
0.7739	Intermediate Similarity	NPD6412	Phase 2
0.7739	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6370	Approved
0.7698	Intermediate Similarity	NPD7736	Approved
0.7679	Intermediate Similarity	NPD7640	Approved
0.7679	Intermediate Similarity	NPD7639	Approved
0.7661	Intermediate Similarity	NPD8328	Phase 3
0.7647	Intermediate Similarity	NPD8133	Approved
0.7642	Intermediate Similarity	NPD7503	Approved
0.7619	Intermediate Similarity	NPD8293	Discontinued
0.7611	Intermediate Similarity	NPD5344	Discontinued
0.7607	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6009	Approved
0.76	Intermediate Similarity	NPD7492	Approved
0.7589	Intermediate Similarity	NPD4225	Approved
0.7563	Intermediate Similarity	NPD6882	Approved
0.7561	Intermediate Similarity	NPD6054	Approved
0.754	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD7115	Discovery
0.7419	Intermediate Similarity	NPD6319	Approved
0.7419	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD8297	Approved
0.7373	Intermediate Similarity	NPD6881	Approved
0.7373	Intermediate Similarity	NPD6899	Approved
0.736	Intermediate Similarity	NPD8515	Approved
0.736	Intermediate Similarity	NPD6015	Approved
0.736	Intermediate Similarity	NPD8513	Phase 3
0.736	Intermediate Similarity	NPD6016	Approved
0.736	Intermediate Similarity	NPD8517	Approved
0.736	Intermediate Similarity	NPD8516	Approved
0.735	Intermediate Similarity	NPD5739	Approved
0.735	Intermediate Similarity	NPD6675	Approved
0.735	Intermediate Similarity	NPD7128	Approved
0.735	Intermediate Similarity	NPD6402	Approved
0.7317	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5988	Approved
0.7288	Intermediate Similarity	NPD5697	Approved
0.725	Intermediate Similarity	NPD7102	Approved
0.725	Intermediate Similarity	NPD7290	Approved
0.725	Intermediate Similarity	NPD6883	Approved
0.7227	Intermediate Similarity	NPD7320	Approved
0.7217	Intermediate Similarity	NPD6648	Approved
0.719	Intermediate Similarity	NPD6649	Approved
0.719	Intermediate Similarity	NPD6869	Approved
0.719	Intermediate Similarity	NPD6617	Approved
0.719	Intermediate Similarity	NPD6650	Approved
0.719	Intermediate Similarity	NPD8130	Phase 1
0.719	Intermediate Similarity	NPD6847	Approved
0.717	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6013	Approved
0.7167	Intermediate Similarity	NPD6012	Approved
0.7167	Intermediate Similarity	NPD6373	Approved
0.7167	Intermediate Similarity	NPD6372	Approved
0.7167	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD5701	Approved
0.7117	Intermediate Similarity	NPD6698	Approved
0.7117	Intermediate Similarity	NPD46	Approved
0.7109	Intermediate Similarity	NPD7604	Phase 2
0.7094	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD5983	Phase 2
0.7087	Intermediate Similarity	NPD6921	Approved
0.7083	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD6336	Discontinued
0.6992	Remote Similarity	NPD6053	Discontinued
0.6977	Remote Similarity	NPD6067	Discontinued
0.6967	Remote Similarity	NPD4634	Approved
0.6967	Remote Similarity	NPD6371	Approved
0.6949	Remote Similarity	NPD5211	Phase 2
0.693	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD5286	Approved
0.6923	Remote Similarity	NPD5285	Approved
0.6923	Remote Similarity	NPD4696	Approved
0.6917	Remote Similarity	NPD6008	Approved
0.6911	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7515	Phase 2
0.6903	Remote Similarity	NPD6079	Approved
0.6897	Remote Similarity	NPD7902	Approved
0.6897	Remote Similarity	NPD4755	Approved
0.6894	Remote Similarity	NPD6033	Approved
0.6875	Remote Similarity	NPD5328	Approved
0.6838	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5141	Approved
0.6825	Remote Similarity	NPD6274	Approved
0.6818	Remote Similarity	NPD8074	Phase 3
0.6807	Remote Similarity	NPD4633	Approved
0.6807	Remote Similarity	NPD5226	Approved
0.6807	Remote Similarity	NPD5225	Approved
0.6807	Remote Similarity	NPD5224	Approved
0.6797	Remote Similarity	NPD7100	Approved
0.6797	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD4700	Approved
0.6774	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6084	Phase 2
0.6752	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD5174	Approved
0.675	Remote Similarity	NPD5175	Approved
0.6727	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5223	Approved
0.6721	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6335	Approved
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD6399	Phase 3
0.6696	Remote Similarity	NPD3573	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD5222	Approved
0.6641	Remote Similarity	NPD6317	Approved
0.6638	Remote Similarity	NPD7900	Approved
0.6638	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5173	Approved
0.6609	Remote Similarity	NPD7983	Approved
0.6607	Remote Similarity	NPD3618	Phase 1
0.6591	Remote Similarity	NPD7829	Approved
0.6591	Remote Similarity	NPD7830	Approved
0.6589	Remote Similarity	NPD6314	Approved
0.6589	Remote Similarity	NPD6313	Approved
0.6581	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6908	Approved
0.6565	Remote Similarity	NPD6909	Approved
0.6562	Remote Similarity	NPD6868	Approved
0.6552	Remote Similarity	NPD7625	Phase 1
0.6552	Remote Similarity	NPD4202	Approved
0.6549	Remote Similarity	NPD7524	Approved
0.6532	Remote Similarity	NPD4729	Approved
0.6532	Remote Similarity	NPD4730	Approved
0.6532	Remote Similarity	NPD5128	Approved
0.6525	Remote Similarity	NPD4697	Phase 3
0.6504	Remote Similarity	NPD4767	Approved
0.6504	Remote Similarity	NPD4768	Approved
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7260	Phase 2
0.6475	Remote Similarity	NPD4754	Approved
0.6466	Remote Similarity	NPD6411	Approved
0.6466	Remote Similarity	NPD7642	Approved
0.6466	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD7637	Suspended
0.6466	Remote Similarity	NPD8035	Phase 2
0.646	Remote Similarity	NPD7521	Approved
0.646	Remote Similarity	NPD7334	Approved
0.646	Remote Similarity	NPD6684	Approved
0.646	Remote Similarity	NPD5330	Approved
0.646	Remote Similarity	NPD7146	Approved
0.646	Remote Similarity	NPD6409	Approved
0.6441	Remote Similarity	NPD5695	Phase 3
0.6439	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5249	Phase 3
0.6429	Remote Similarity	NPD5250	Approved
0.6429	Remote Similarity	NPD5251	Approved
0.6429	Remote Similarity	NPD5248	Approved
0.6429	Remote Similarity	NPD5247	Approved
0.6423	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5696	Approved
0.6378	Remote Similarity	NPD5217	Approved
0.6378	Remote Similarity	NPD5215	Approved
0.6378	Remote Similarity	NPD5216	Approved
0.6372	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.637	Remote Similarity	NPD8451	Approved
0.6348	Remote Similarity	NPD5737	Approved
0.6348	Remote Similarity	NPD6672	Approved
0.6348	Remote Similarity	NPD6903	Approved
0.6348	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7641	Discontinued
0.6331	Remote Similarity	NPD8338	Approved
0.6325	Remote Similarity	NPD5693	Phase 1
0.6324	Remote Similarity	NPD8448	Approved
0.6304	Remote Similarity	NPD5956	Approved
0.6304	Remote Similarity	NPD6914	Discontinued
0.6303	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5169	Approved
0.6299	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5135	Approved
0.6296	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4753	Phase 2
0.6293	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6101	Approved
0.6283	Remote Similarity	NPD4786	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