NPASS Compound

Structure

NPC108026 OpenBabel07101718322D 32 33 0 0 0 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 26 29 2 0 0 0 0 27 28 2 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.26
Volume:	487.164
LogP:	5.173
LogD:	4.668
LogS:	-5.198
# Rotatable Bonds:	11
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	3.305
Fsp3:	0.393
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:	-4.613
MDCK Permeability:	1.8920962247648276e-05
Pgp-inhibitor:	0.925
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	96.87520599365234%
Volume Distribution (VD):	0.131
Pgp-substrate:	0.45782938599586487%

ADMET: Metabolism

CYP1A2-inhibitor:	0.551
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.958
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.349
CYP2D6-substrate:	0.773
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	3.77
Half-life (T1/2):	0.411

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.854
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.342
Skin Sensitization:	0.963
Carcinogencity:	0.049
Eye Corrosion:	0.004
Eye Irritation:	0.158
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC108026

Natural Product ID:	NPC108026
*Common Name:**	Lehualide B
IUPAC Name:	2,3-dimethoxy-5-methyl-6-[(2E,6Z,9E)-3,7,9-trimethyl-11-phenylundeca-2,6,9-trienyl]pyran-4-one
Synonyms:
Standard InCHIKey:	YVIWNCQQXZJAHK-DXYHPHEZSA-N
Standard InCHI:	InChI=1S/C28H36O4/c1-20(16-18-25-23(4)26(29)27(30-5)28(31-6)32-25)11-10-12-21(2)19-22(3)15-17-24-13-8-7-9-14-24/h7-9,12-16H,10-11,17-19H2,1-6H3/b20-16+,21-12-,22-15+
SMILES:	COc1oc(C/C=C(/CC/C=C(C/C(=C/Cc2ccccc2)/C)/C)C)c(c(=O)c1OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464742
PubChem CID:	11517742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO31509	Plakortis	Genus	Plakinidae	Eukaryota	n.a.	Hawaiian	n.a.	PMID[16180823]
NPO31509	Plakortis	Genus	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21351759]

☑ 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
GI50	1
LD50	1

Activity Type	# Activity
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	15.0	ug ml-1	PMID[470564]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	830.0	nM	PMID[470564]

☑ 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 NPC108026 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	367
0.1-0.2	1611
0.2-0.3	4532
0.3-0.4	10400
0.4-0.5	8393
0.5-0.6	5229
0.6-0.7	7952
0.7-0.8	4175
0.8-0.85	34
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC103048
0.8065	Intermediate Similarity	NPC67585
0.8065	Intermediate Similarity	NPC110420
0.8065	Intermediate Similarity	NPC303967
0.8041	Intermediate Similarity	NPC145052
0.8041	Intermediate Similarity	NPC135951
0.7979	Intermediate Similarity	NPC476484
0.7959	Intermediate Similarity	NPC80115
0.7917	Intermediate Similarity	NPC473347
0.7912	Intermediate Similarity	NPC53299
0.7857	Intermediate Similarity	NPC154517
0.7835	Intermediate Similarity	NPC12695
0.7714	Intermediate Similarity	NPC477247
0.7582	Intermediate Similarity	NPC99240
0.757	Intermediate Similarity	NPC477245
0.757	Intermediate Similarity	NPC477246
0.7553	Intermediate Similarity	NPC96625
0.7553	Intermediate Similarity	NPC169050
0.7553	Intermediate Similarity	NPC286608
0.7477	Intermediate Similarity	NPC477250
0.7449	Intermediate Similarity	NPC23453
0.7416	Intermediate Similarity	NPC179726
0.7412	Intermediate Similarity	NPC98880
0.7374	Intermediate Similarity	NPC5472
0.7353	Intermediate Similarity	NPC112552
0.7347	Intermediate Similarity	NPC77273
0.7333	Intermediate Similarity	NPC477251
0.7326	Intermediate Similarity	NPC95289
0.7294	Intermediate Similarity	NPC311343
0.7283	Intermediate Similarity	NPC71795
0.7273	Intermediate Similarity	NPC34243
0.7253	Intermediate Similarity	NPC139901
0.7253	Intermediate Similarity	NPC151405
0.7228	Intermediate Similarity	NPC278228
0.7228	Intermediate Similarity	NPC240042
0.7204	Intermediate Similarity	NPC323103
0.7204	Intermediate Similarity	NPC103387
0.7174	Intermediate Similarity	NPC121800
0.7158	Intermediate Similarity	NPC123476
0.7158	Intermediate Similarity	NPC475710
0.7157	Intermediate Similarity	NPC476120
0.7157	Intermediate Similarity	NPC179411
0.7128	Intermediate Similarity	NPC324835
0.7128	Intermediate Similarity	NPC270507
0.7128	Intermediate Similarity	NPC308619
0.7128	Intermediate Similarity	NPC127491
0.7113	Intermediate Similarity	NPC477693
0.7113	Intermediate Similarity	NPC477704
0.7103	Intermediate Similarity	NPC47536
0.7091	Intermediate Similarity	NPC469547
0.7087	Intermediate Similarity	NPC474308
0.7065	Intermediate Similarity	NPC272260
0.7065	Intermediate Similarity	NPC170484
0.7065	Intermediate Similarity	NPC300205
0.7059	Intermediate Similarity	NPC472788
0.7045	Intermediate Similarity	NPC74458
0.7045	Intermediate Similarity	NPC326200
0.7041	Intermediate Similarity	NPC231591
0.7037	Intermediate Similarity	NPC40178
0.7033	Intermediate Similarity	NPC287790
0.7033	Intermediate Similarity	NPC3672
0.7033	Intermediate Similarity	NPC9796
0.701	Intermediate Similarity	NPC69057
0.6989	Remote Similarity	NPC285716
0.6989	Remote Similarity	NPC164086
0.6989	Remote Similarity	NPC17408
0.697	Remote Similarity	NPC240108
0.697	Remote Similarity	NPC213156
0.6966	Remote Similarity	NPC285679
0.6964	Remote Similarity	NPC472164
0.6964	Remote Similarity	NPC474408
0.6961	Remote Similarity	NPC30361
0.6957	Remote Similarity	NPC76455
0.6957	Remote Similarity	NPC285470
0.6957	Remote Similarity	NPC2785
0.6957	Remote Similarity	NPC36342
0.6957	Remote Similarity	NPC137847
0.6947	Remote Similarity	NPC288903
0.6947	Remote Similarity	NPC208183
0.6947	Remote Similarity	NPC243289
0.6944	Remote Similarity	NPC470007
0.6944	Remote Similarity	NPC203732
0.6944	Remote Similarity	NPC470391
0.6937	Remote Similarity	NPC477475
0.6937	Remote Similarity	NPC477476
0.6923	Remote Similarity	NPC476042
0.6915	Remote Similarity	NPC303245
0.6915	Remote Similarity	NPC89950
0.6909	Remote Similarity	NPC137315
0.69	Remote Similarity	NPC284475
0.6882	Remote Similarity	NPC167577
0.6882	Remote Similarity	NPC78517
0.6881	Remote Similarity	NPC192577
0.6875	Remote Similarity	NPC326664
0.6869	Remote Similarity	NPC9822
0.6854	Remote Similarity	NPC155429
0.6848	Remote Similarity	NPC329318
0.6848	Remote Similarity	NPC245966
0.6837	Remote Similarity	NPC194326
0.6832	Remote Similarity	NPC188844
0.6832	Remote Similarity	NPC1682
0.6827	Remote Similarity	NPC475954
0.6818	Remote Similarity	NPC16190
0.6818	Remote Similarity	NPC273837
0.6818	Remote Similarity	NPC169222
0.6818	Remote Similarity	NPC235059
0.6809	Remote Similarity	NPC190567
0.6809	Remote Similarity	NPC477703
0.6809	Remote Similarity	NPC71664
0.6809	Remote Similarity	NPC95868
0.6807	Remote Similarity	NPC473942
0.6804	Remote Similarity	NPC95965
0.6804	Remote Similarity	NPC294134
0.68	Remote Similarity	NPC84288
0.6789	Remote Similarity	NPC20485
0.6786	Remote Similarity	NPC161611
0.6783	Remote Similarity	NPC471553
0.6774	Remote Similarity	NPC103488
0.6774	Remote Similarity	NPC475569
0.6774	Remote Similarity	NPC176228
0.6771	Remote Similarity	NPC477770
0.6771	Remote Similarity	NPC273758
0.6762	Remote Similarity	NPC54647
0.6757	Remote Similarity	NPC291799
0.6754	Remote Similarity	NPC235421
0.6739	Remote Similarity	NPC175393
0.6737	Remote Similarity	NPC73978
0.6737	Remote Similarity	NPC273033
0.6737	Remote Similarity	NPC145053
0.6737	Remote Similarity	NPC12936
0.6733	Remote Similarity	NPC110704
0.6731	Remote Similarity	NPC289201
0.6729	Remote Similarity	NPC474365
0.6729	Remote Similarity	NPC301943
0.6727	Remote Similarity	NPC281604
0.6726	Remote Similarity	NPC67377
0.6702	Remote Similarity	NPC469894
0.6701	Remote Similarity	NPC267704
0.6701	Remote Similarity	NPC44546
0.67	Remote Similarity	NPC173443
0.6696	Remote Similarity	NPC108532
0.6696	Remote Similarity	NPC325646
0.6696	Remote Similarity	NPC28951
0.6667	Remote Similarity	NPC475057
0.6667	Remote Similarity	NPC269644
0.6667	Remote Similarity	NPC43945
0.6667	Remote Similarity	NPC155232
0.6667	Remote Similarity	NPC210092
0.6667	Remote Similarity	NPC109637
0.6667	Remote Similarity	NPC59677
0.6667	Remote Similarity	NPC473881
0.6667	Remote Similarity	NPC153885
0.6636	Remote Similarity	NPC244427
0.6636	Remote Similarity	NPC222390
0.6632	Remote Similarity	NPC309279
0.663	Remote Similarity	NPC206800
0.663	Remote Similarity	NPC32203
0.6612	Remote Similarity	NPC472165
0.661	Remote Similarity	NPC475827
0.661	Remote Similarity	NPC474223
0.661	Remote Similarity	NPC473243
0.6609	Remote Similarity	NPC471616
0.6609	Remote Similarity	NPC216387
0.6607	Remote Similarity	NPC474157
0.6606	Remote Similarity	NPC474307
0.6606	Remote Similarity	NPC127676
0.6606	Remote Similarity	NPC209632
0.6604	Remote Similarity	NPC7435
0.6602	Remote Similarity	NPC238219
0.66	Remote Similarity	NPC157778
0.66	Remote Similarity	NPC304760
0.6598	Remote Similarity	NPC215008
0.6598	Remote Similarity	NPC44830
0.6596	Remote Similarity	NPC50192
0.6593	Remote Similarity	NPC271437
0.6588	Remote Similarity	NPC210849
0.6579	Remote Similarity	NPC241851
0.6577	Remote Similarity	NPC475282
0.6577	Remote Similarity	NPC469636
0.6577	Remote Similarity	NPC469511
0.6574	Remote Similarity	NPC274443
0.6574	Remote Similarity	NPC234305
0.6571	Remote Similarity	NPC156021
0.6571	Remote Similarity	NPC270654
0.6571	Remote Similarity	NPC477767
0.6569	Remote Similarity	NPC141607
0.6569	Remote Similarity	NPC475023
0.6569	Remote Similarity	NPC475059
0.6569	Remote Similarity	NPC133461
0.6569	Remote Similarity	NPC119631
0.6569	Remote Similarity	NPC187725
0.6569	Remote Similarity	NPC472319
0.6569	Remote Similarity	NPC317645
0.6549	Remote Similarity	NPC474689
0.6549	Remote Similarity	NPC470355
0.6549	Remote Similarity	NPC292834
0.6545	Remote Similarity	NPC51174
0.6545	Remote Similarity	NPC472315
0.6545	Remote Similarity	NPC475203
0.6545	Remote Similarity	NPC474376

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 NPC108026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	920
0.2-0.3	1649
0.3-0.4	2807
0.4-0.5	1917
0.5-0.6	1105
0.6-0.7	322
0.7-0.8	97
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7553	Intermediate Similarity	NPD1282	Approved
0.713	Intermediate Similarity	NPD2067	Discontinued
0.71	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3971	Phase 1
0.69	Remote Similarity	NPD7609	Phase 3
0.6887	Remote Similarity	NPD6647	Phase 2
0.6832	Remote Similarity	NPD7631	Approved
0.6822	Remote Similarity	NPD5909	Discontinued
0.6809	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD2066	Phase 3
0.6737	Remote Similarity	NPD942	Approved
0.6667	Remote Similarity	NPD5926	Approved
0.6667	Remote Similarity	NPD650	Approved
0.6635	Remote Similarity	NPD1989	Approved
0.6634	Remote Similarity	NPD3672	Approved
0.6634	Remote Similarity	NPD3673	Approved
0.663	Remote Similarity	NPD9716	Approved
0.6604	Remote Similarity	NPD7798	Approved
0.6596	Remote Similarity	NPD227	Approved
0.6596	Remote Similarity	NPD225	Approved
0.6535	Remote Similarity	NPD5346	Phase 2
0.6535	Remote Similarity	NPD689	Discontinued
0.6535	Remote Similarity	NPD5347	Phase 2
0.6526	Remote Similarity	NPD9490	Approved
0.6522	Remote Similarity	NPD690	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1087	Approved
0.65	Remote Similarity	NPD4793	Discontinued
0.6436	Remote Similarity	NPD531	Approved
0.6429	Remote Similarity	NPD9491	Approved
0.6422	Remote Similarity	NPD1930	Approved
0.6422	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1929	Approved
0.6415	Remote Similarity	NPD3495	Discontinued
0.6404	Remote Similarity	NPD969	Suspended
0.6396	Remote Similarity	NPD3134	Approved
0.6392	Remote Similarity	NPD226	Approved
0.6389	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD1693	Approved
0.6381	Remote Similarity	NPD6049	Phase 2
0.6373	Remote Similarity	NPD800	Approved
0.6364	Remote Similarity	NPD1237	Approved
0.6348	Remote Similarity	NPD7094	Approved
0.6348	Remote Similarity	NPD6858	Approved
0.6339	Remote Similarity	NPD1358	Approved
0.6337	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4198	Discontinued
0.6311	Remote Similarity	NPD1086	Approved
0.6311	Remote Similarity	NPD1090	Approved
0.6311	Remote Similarity	NPD1089	Approved
0.6306	Remote Similarity	NPD5048	Discontinued
0.6286	Remote Similarity	NPD1202	Approved
0.6283	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD2182	Approved
0.6273	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6685	Approved
0.625	Remote Similarity	NPD1007	Discontinued
0.6218	Remote Similarity	NPD5536	Phase 2
0.6216	Remote Similarity	NPD164	Approved
0.6204	Remote Similarity	NPD9495	Approved
0.619	Remote Similarity	NPD1088	Approved
0.619	Remote Similarity	NPD1508	Approved
0.6182	Remote Similarity	NPD1932	Approved
0.6174	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1241	Discontinued
0.6147	Remote Similarity	NPD1238	Approved
0.6132	Remote Similarity	NPD1066	Discontinued
0.6132	Remote Similarity	NPD1563	Approved
0.6126	Remote Similarity	NPD5765	Approved
0.6111	Remote Similarity	NPD2798	Approved
0.6111	Remote Similarity	NPD2788	Approved
0.6106	Remote Similarity	NPD5705	Approved
0.6106	Remote Similarity	NPD5706	Approved
0.6106	Remote Similarity	NPD5704	Approved
0.6102	Remote Similarity	NPD2629	Approved
0.6095	Remote Similarity	NPD1239	Approved
0.6078	Remote Similarity	NPD9257	Approved
0.6078	Remote Similarity	NPD9259	Approved
0.6077	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4094	Approved
0.6075	Remote Similarity	NPD2933	Approved
0.6075	Remote Similarity	NPD2934	Approved
0.6068	Remote Similarity	NPD5535	Approved
0.6067	Remote Similarity	NPD675	Discontinued
0.6053	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6387	Discontinued
0.6036	Remote Similarity	NPD2648	Phase 3
0.6036	Remote Similarity	NPD2171	Approved
0.6036	Remote Similarity	NPD2193	Phase 2
0.6019	Remote Similarity	NPD2859	Approved
0.6019	Remote Similarity	NPD2860	Approved
0.6019	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1843	Approved
0.6018	Remote Similarity	NPD9697	Approved
0.6	Remote Similarity	NPD2329	Discontinued
0.5983	Remote Similarity	NPD1137	Approved
0.5983	Remote Similarity	NPD1139	Approved
0.5982	Remote Similarity	NPD3357	Discontinued
0.5968	Remote Similarity	NPD6287	Discontinued
0.5963	Remote Similarity	NPD1566	Phase 3
0.5963	Remote Similarity	NPD1565	Approved
0.5963	Remote Similarity	NPD4655	Approved
0.5963	Remote Similarity	NPD1099	Approved
0.5963	Remote Similarity	NPD1564	Approved
0.5963	Remote Similarity	NPD4657	Approved
0.5963	Remote Similarity	NPD1100	Approved
0.5948	Remote Similarity	NPD5235	Approved
0.5948	Remote Similarity	NPD5237	Approved
0.5948	Remote Similarity	NPD5239	Approved
0.5948	Remote Similarity	NPD5240	Approved
0.5948	Remote Similarity	NPD5236	Approved
0.5948	Remote Similarity	NPD1317	Discontinued
0.5946	Remote Similarity	NPD3028	Approved
0.5935	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD1138	Approved
0.5926	Remote Similarity	NPD7344	Phase 1
0.5926	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD688	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7343	Discovery
0.592	Remote Similarity	NPD6637	Approved
0.592	Remote Similarity	NPD3972	Approved
0.5914	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD3266	Approved
0.5906	Remote Similarity	NPD3267	Approved
0.5902	Remote Similarity	NPD4479	Discontinued
0.5899	Remote Similarity	NPD3950	Discontinued
0.5897	Remote Similarity	NPD2201	Approved
0.5893	Remote Similarity	NPD2196	Discontinued
0.5891	Remote Similarity	NPD6832	Phase 2
0.5887	Remote Similarity	NPD3496	Discontinued
0.5887	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD3847	Discontinued
0.5878	Remote Similarity	NPD7961	Discontinued
0.5873	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD694	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3020	Approved
0.5854	Remote Similarity	NPD5691	Approved
0.5849	Remote Similarity	NPD9258	Approved
0.5849	Remote Similarity	NPD9256	Approved
0.5847	Remote Similarity	NPD6912	Phase 3
0.5846	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD7095	Approved
0.584	Remote Similarity	NPD4806	Approved
0.584	Remote Similarity	NPD4807	Approved
0.5833	Remote Similarity	NPD720	Approved
0.5833	Remote Similarity	NPD3718	Approved
0.5833	Remote Similarity	NPD719	Approved
0.5833	Remote Similarity	NPD3719	Approved
0.5824	Remote Similarity	NPD173	Clinical (unspecified phase)
0.582	Remote Similarity	NPD2347	Approved
0.5818	Remote Similarity	NPD1076	Approved
0.5816	Remote Similarity	NPD4144	Approved
0.5816	Remote Similarity	NPD9294	Approved
0.5816	Remote Similarity	NPD4147	Approved
0.5812	Remote Similarity	NPD1756	Approved
0.5812	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4234	Approved
0.5812	Remote Similarity	NPD5451	Approved
0.5812	Remote Similarity	NPD1752	Approved
0.5812	Remote Similarity	NPD4233	Approved
0.581	Remote Similarity	NPD1101	Approved
0.5806	Remote Similarity	NPD4626	Approved
0.5806	Remote Similarity	NPD5305	Approved
0.5806	Remote Similarity	NPD5306	Approved
0.5804	Remote Similarity	NPD2549	Approved
0.5804	Remote Similarity	NPD2550	Approved
0.5804	Remote Similarity	NPD2558	Approved
0.5804	Remote Similarity	NPD2553	Approved
0.5804	Remote Similarity	NPD2555	Approved
0.5804	Remote Similarity	NPD2552	Approved
0.5802	Remote Similarity	NPD6798	Discontinued
0.5802	Remote Similarity	NPD3268	Approved
0.5798	Remote Similarity	NPD7843	Approved
0.5798	Remote Similarity	NPD2607	Approved
0.5789	Remote Similarity	NPD6355	Discontinued
0.5789	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4340	Discontinued
0.5785	Remote Similarity	NPD7508	Discontinued
0.5781	Remote Similarity	NPD2797	Approved
0.578	Remote Similarity	NPD4814	Discontinued
0.5776	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4813	Approved
0.5766	Remote Similarity	NPD4263	Approved
0.5766	Remote Similarity	NPD1724	Approved
0.576	Remote Similarity	NPD4879	Approved
0.576	Remote Similarity	NPD4136	Approved
0.576	Remote Similarity	NPD4106	Approved
0.576	Remote Similarity	NPD4135	Approved
0.5758	Remote Similarity	NPD6233	Phase 2
0.5758	Remote Similarity	NPD4062	Phase 3
0.5752	Remote Similarity	NPD4189	Approved
0.5752	Remote Similarity	NPD6027	Approved
0.5752	Remote Similarity	NPD6024	Approved
0.5752	Remote Similarity	NPD4188	Approved
0.575	Remote Similarity	NPD2652	Approved
0.575	Remote Similarity	NPD7077	Approved
0.575	Remote Similarity	NPD2650	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