NPASS Compound

Structure

NPC469911 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.6846 3.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4499 2.8129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0060 -4.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6654 -3.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 -1.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9305 3.7440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9558 2.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3833 -1.3994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9582 3.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9083 -0.7019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2487 1.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9558 -2.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2487 -1.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8934 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5107 1.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8797 2.5137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4530 2.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5107 -1.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8934 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8797 2.5137 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.8036 2.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6902 0.1434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8797 -2.5137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8036 -2.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6846 -3.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4542 0.7886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3591 -2.9625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 -3.8159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8797 -2.5137 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 20 21 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 1 0 0 0 23 31 1 0 0 0 0 24 27 1 6 0 0 0 24 32 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 30 1 0 0 0 0 27 5 1 6 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.26
Volume:	469.455
LogP:	5.073
LogD:	3.741
LogS:	-3.999
# Rotatable Bonds:	1
TPSA:	79.29
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	5.718
Fsp3:	0.593
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:	-4.602
MDCK Permeability:	2.951172245957423e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.207
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.298

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	98.37067413330078%
Volume Distribution (VD):	1.555
Pgp-substrate:	1.2897380590438843%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.178
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.332
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.741
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	9.391
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.342
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.465
Carcinogencity:	0.216
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.745

Download Data

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

Natural Product: NPC469911

Natural Product ID:	NPC469911
*Common Name:**	XHVNCHKVWKNRKD-FHCFCJHCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XHVNCHKVWKNRKD-FHCFCJHCSA-N
Standard InCHI:	InChI=1S/C27H36O5/c1-16-7-11-24-27(5,32-24)13-12-23(26(3,4)30)31-25(29)18-8-10-22(28)19(14-18)15-21-17(2)6-9-20(16)21/h7-8,10,14,20,23-24,28,30H,6,9,11-13,15H2,1-5H3/b16-7+/t20?,23-,24-,27-/m0/s1
SMILES:	CC1=C2CC3=C(C=CC(=C3)C(=O)OC(CCC4(C(O4)CC=C(C2CC1)C)C)C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258082
PubChem CID:	21778347
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33001	macroalgae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20801038]

☑ 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
MIC	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	100000.0	nM	PMID[473105]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	100000.0	nM	PMID[473105]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500000.0	nM	PMID[473105]

☑ 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 NPC469911 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	305
0.1-0.2	1196
0.2-0.3	2803
0.3-0.4	6728
0.4-0.5	10791
0.5-0.6	5837
0.6-0.7	9757
0.7-0.8	5168
0.8-0.85	98
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC302844
0.9179	High Similarity	NPC473777
0.8955	High Similarity	NPC473744
0.8844	High Similarity	NPC475093
0.8803	High Similarity	NPC184053
0.8797	High Similarity	NPC184219
0.8667	High Similarity	NPC204579
0.8647	High Similarity	NPC67300
0.8639	High Similarity	NPC17600
0.8613	High Similarity	NPC194979
0.8591	High Similarity	NPC11892
0.8582	High Similarity	NPC475111
0.8581	High Similarity	NPC52931
0.8529	High Similarity	NPC110211
0.8523	High Similarity	NPC37642
0.8507	High Similarity	NPC475192
0.8503	High Similarity	NPC469498
0.85	High Similarity	NPC239855
0.8467	Intermediate Similarity	NPC121104
0.8456	Intermediate Similarity	NPC49938
0.844	Intermediate Similarity	NPC204582
0.8435	Intermediate Similarity	NPC97188
0.8392	Intermediate Similarity	NPC170718
0.8389	Intermediate Similarity	NPC161955
0.8367	Intermediate Similarity	NPC213900
0.8345	Intermediate Similarity	NPC64664
0.8322	Intermediate Similarity	NPC14875
0.8311	Intermediate Similarity	NPC83272
0.8299	Intermediate Similarity	NPC469615
0.8289	Intermediate Similarity	NPC229354
0.8278	Intermediate Similarity	NPC289021
0.8278	Intermediate Similarity	NPC158546
0.8271	Intermediate Similarity	NPC27633
0.8271	Intermediate Similarity	NPC273282
0.8271	Intermediate Similarity	NPC94298
0.8271	Intermediate Similarity	NPC474890
0.8271	Intermediate Similarity	NPC161943
0.8255	Intermediate Similarity	NPC473023
0.8243	Intermediate Similarity	NPC469683
0.8239	Intermediate Similarity	NPC477280
0.8239	Intermediate Similarity	NPC19719
0.8239	Intermediate Similarity	NPC477281
0.8239	Intermediate Similarity	NPC114116
0.8231	Intermediate Similarity	NPC478250
0.8214	Intermediate Similarity	NPC226855
0.82	Intermediate Similarity	NPC66991
0.82	Intermediate Similarity	NPC189631
0.82	Intermediate Similarity	NPC81835
0.8188	Intermediate Similarity	NPC208293
0.8188	Intermediate Similarity	NPC470857
0.8188	Intermediate Similarity	NPC75295
0.8188	Intermediate Similarity	NPC258856
0.8176	Intermediate Similarity	NPC271451
0.8176	Intermediate Similarity	NPC77922
0.8176	Intermediate Similarity	NPC473281
0.817	Intermediate Similarity	NPC256141
0.8169	Intermediate Similarity	NPC323379
0.8169	Intermediate Similarity	NPC470859
0.8169	Intermediate Similarity	NPC327204
0.8158	Intermediate Similarity	NPC56204
0.8158	Intermediate Similarity	NPC180351
0.8158	Intermediate Similarity	NPC472421
0.8156	Intermediate Similarity	NPC327457
0.8156	Intermediate Similarity	NPC86774
0.8156	Intermediate Similarity	NPC109778
0.8153	Intermediate Similarity	NPC92589
0.8146	Intermediate Similarity	NPC279442
0.8143	Intermediate Similarity	NPC217431
0.8143	Intermediate Similarity	NPC2596
0.8138	Intermediate Similarity	NPC477592
0.8133	Intermediate Similarity	NPC286038
0.8133	Intermediate Similarity	NPC316769
0.8129	Intermediate Similarity	NPC473751
0.8129	Intermediate Similarity	NPC321372
0.8129	Intermediate Similarity	NPC469936
0.8129	Intermediate Similarity	NPC474609
0.8129	Intermediate Similarity	NPC475797
0.8129	Intermediate Similarity	NPC474945
0.8129	Intermediate Similarity	NPC129053
0.8129	Intermediate Similarity	NPC109967
0.8129	Intermediate Similarity	NPC476022
0.8129	Intermediate Similarity	NPC474738
0.8129	Intermediate Similarity	NPC78554
0.8121	Intermediate Similarity	NPC126882
0.8121	Intermediate Similarity	NPC210966
0.8121	Intermediate Similarity	NPC478203
0.8121	Intermediate Similarity	NPC113397
0.812	Intermediate Similarity	NPC83718
0.812	Intermediate Similarity	NPC131192
0.8105	Intermediate Similarity	NPC474744
0.8105	Intermediate Similarity	NPC478235
0.8105	Intermediate Similarity	NPC472423
0.8105	Intermediate Similarity	NPC474772
0.8105	Intermediate Similarity	NPC194705
0.8099	Intermediate Similarity	NPC470976
0.8099	Intermediate Similarity	NPC15083
0.8099	Intermediate Similarity	NPC470977
0.8099	Intermediate Similarity	NPC196979
0.8095	Intermediate Similarity	NPC158472
0.8095	Intermediate Similarity	NPC327187
0.8095	Intermediate Similarity	NPC51181
0.8092	Intermediate Similarity	NPC267469
0.8092	Intermediate Similarity	NPC87630
0.8092	Intermediate Similarity	NPC162569
0.8092	Intermediate Similarity	NPC116292
0.8092	Intermediate Similarity	NPC327962
0.8092	Intermediate Similarity	NPC104172
0.8092	Intermediate Similarity	NPC179128
0.8092	Intermediate Similarity	NPC142654
0.8092	Intermediate Similarity	NPC35160
0.8092	Intermediate Similarity	NPC88886
0.8092	Intermediate Similarity	NPC247219
0.8082	Intermediate Similarity	NPC477593
0.8082	Intermediate Similarity	NPC221104
0.8082	Intermediate Similarity	NPC112135
0.8079	Intermediate Similarity	NPC473133
0.8079	Intermediate Similarity	NPC53362
0.8079	Intermediate Similarity	NPC91902
0.8079	Intermediate Similarity	NPC166583
0.8079	Intermediate Similarity	NPC47388
0.8079	Intermediate Similarity	NPC470670
0.8074	Intermediate Similarity	NPC473767
0.8071	Intermediate Similarity	NPC158654
0.8069	Intermediate Similarity	NPC156892
0.8069	Intermediate Similarity	NPC291454
0.8069	Intermediate Similarity	NPC326847
0.8067	Intermediate Similarity	NPC257558
0.8067	Intermediate Similarity	NPC474044
0.8065	Intermediate Similarity	NPC108937
0.8065	Intermediate Similarity	NPC279218
0.8056	Intermediate Similarity	NPC477594
0.8054	Intermediate Similarity	NPC202391
0.8054	Intermediate Similarity	NPC130206
0.8054	Intermediate Similarity	NPC296659
0.8052	Intermediate Similarity	NPC327269
0.8052	Intermediate Similarity	NPC476238
0.8052	Intermediate Similarity	NPC477957
0.8052	Intermediate Similarity	NPC31627
0.8052	Intermediate Similarity	NPC131121
0.8052	Intermediate Similarity	NPC473996
0.8052	Intermediate Similarity	NPC257847
0.8043	Intermediate Similarity	NPC174991
0.8041	Intermediate Similarity	NPC470842
0.8041	Intermediate Similarity	NPC477595
0.8039	Intermediate Similarity	NPC243891
0.8039	Intermediate Similarity	NPC321387
0.8039	Intermediate Similarity	NPC327059
0.8039	Intermediate Similarity	NPC469670
0.8039	Intermediate Similarity	NPC470908
0.8039	Intermediate Similarity	NPC179178
0.8039	Intermediate Similarity	NPC474620
0.8039	Intermediate Similarity	NPC469619
0.8038	Intermediate Similarity	NPC469889
0.8028	Intermediate Similarity	NPC282230
0.8028	Intermediate Similarity	NPC183348
0.8028	Intermediate Similarity	NPC163169
0.8028	Intermediate Similarity	NPC123
0.8027	Intermediate Similarity	NPC473988
0.8027	Intermediate Similarity	NPC475012
0.8026	Intermediate Similarity	NPC94781
0.8026	Intermediate Similarity	NPC478236
0.8026	Intermediate Similarity	NPC478234
0.8014	Intermediate Similarity	NPC71256
0.8014	Intermediate Similarity	NPC194579
0.8014	Intermediate Similarity	NPC70380
0.8014	Intermediate Similarity	NPC2401
0.8014	Intermediate Similarity	NPC229894
0.8013	Intermediate Similarity	NPC471787
0.8013	Intermediate Similarity	NPC473149
0.8013	Intermediate Similarity	NPC229264
0.8	Intermediate Similarity	NPC475236
0.8	Intermediate Similarity	NPC29317
0.8	Intermediate Similarity	NPC151607
0.8	Intermediate Similarity	NPC233350
0.8	Intermediate Similarity	NPC267539
0.8	Intermediate Similarity	NPC254832
0.8	Intermediate Similarity	NPC475011
0.8	Intermediate Similarity	NPC204257
0.8	Intermediate Similarity	NPC62051
0.8	Intermediate Similarity	NPC18646
0.8	Intermediate Similarity	NPC42540
0.8	Intermediate Similarity	NPC229638
0.8	Intermediate Similarity	NPC475029
0.8	Intermediate Similarity	NPC182217
0.8	Intermediate Similarity	NPC176102
0.8	Intermediate Similarity	NPC476018
0.8	Intermediate Similarity	NPC474944
0.8	Intermediate Similarity	NPC71108
0.8	Intermediate Similarity	NPC477596
0.8	Intermediate Similarity	NPC70680
0.8	Intermediate Similarity	NPC210330
0.7987	Intermediate Similarity	NPC74397
0.7987	Intermediate Similarity	NPC48671
0.7987	Intermediate Similarity	NPC471675
0.7987	Intermediate Similarity	NPC472580
0.7987	Intermediate Similarity	NPC124842
0.7987	Intermediate Similarity	NPC471677
0.7987	Intermediate Similarity	NPC240768
0.7987	Intermediate Similarity	NPC263384
0.7987	Intermediate Similarity	NPC472420

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 NPC469911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	819
0.2-0.3	1661
0.3-0.4	2570
0.4-0.5	2102
0.5-0.6	1169
0.6-0.7	503
0.7-0.8	67
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
0.8271	Intermediate Similarity	NPD9545	Approved
0.8041	Intermediate Similarity	NPD4628	Phase 3
0.7973	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7075	Discontinued
0.7885	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD230	Phase 1
0.7806	Intermediate Similarity	NPD4380	Phase 2
0.7778	Intermediate Similarity	NPD3764	Approved
0.7651	Intermediate Similarity	NPD2935	Discontinued
0.7628	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD6355	Discontinued
0.7597	Intermediate Similarity	NPD2534	Approved
0.7597	Intermediate Similarity	NPD2533	Approved
0.7597	Intermediate Similarity	NPD2532	Approved
0.7595	Intermediate Similarity	NPD6801	Discontinued
0.7562	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6799	Approved
0.7516	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7467	Intermediate Similarity	NPD2799	Discontinued
0.7464	Intermediate Similarity	NPD9493	Approved
0.7444	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7819	Suspended
0.7434	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7411	Suspended
0.7415	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1934	Approved
0.7358	Intermediate Similarity	NPD6599	Discontinued
0.7351	Intermediate Similarity	NPD1510	Phase 2
0.7346	Intermediate Similarity	NPD7768	Phase 2
0.7326	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5844	Phase 1
0.732	Intermediate Similarity	NPD1549	Phase 2
0.7315	Intermediate Similarity	NPD1240	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7261	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3882	Suspended
0.7237	Intermediate Similarity	NPD7033	Discontinued
0.7229	Intermediate Similarity	NPD6232	Discontinued
0.7226	Intermediate Similarity	NPD3750	Approved
0.7226	Intermediate Similarity	NPD8166	Discontinued
0.7226	Intermediate Similarity	NPD7003	Approved
0.7226	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1607	Approved
0.7211	Intermediate Similarity	NPD9494	Approved
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.72	Intermediate Similarity	NPD4060	Phase 1
0.7193	Intermediate Similarity	NPD6559	Discontinued
0.719	Intermediate Similarity	NPD2796	Approved
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD3817	Phase 2
0.717	Intermediate Similarity	NPD920	Approved
0.716	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7134	Intermediate Similarity	NPD7236	Approved
0.7133	Intermediate Similarity	NPD6663	Approved
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2801	Approved
0.7117	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5494	Approved
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7107	Intermediate Similarity	NPD6273	Approved
0.7105	Intermediate Similarity	NPD6651	Approved
0.7105	Intermediate Similarity	NPD6653	Approved
0.7103	Intermediate Similarity	NPD1608	Approved
0.7103	Intermediate Similarity	NPD9269	Phase 2
0.7103	Intermediate Similarity	NPD9717	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5736	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD3455	Phase 2
0.7081	Intermediate Similarity	NPD3226	Approved
0.7078	Intermediate Similarity	NPD1551	Phase 2
0.7076	Intermediate Similarity	NPD7074	Phase 3
0.7075	Intermediate Similarity	NPD1164	Approved
0.7071	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3887	Approved
0.707	Intermediate Similarity	NPD2354	Approved
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD5403	Approved
0.7059	Intermediate Similarity	NPD7097	Phase 1
0.7051	Intermediate Similarity	NPD1243	Approved
0.7051	Intermediate Similarity	NPD2800	Approved
0.7047	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6166	Phase 2
0.7039	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5763	Approved
0.7032	Intermediate Similarity	NPD5762	Approved
0.7032	Intermediate Similarity	NPD2344	Approved
0.7029	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5647	Approved
0.7025	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD7286	Phase 2
0.7018	Intermediate Similarity	NPD7054	Approved
0.7014	Intermediate Similarity	NPD4626	Approved
0.7013	Intermediate Similarity	NPD4308	Phase 3
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.6994	Remote Similarity	NPD6385	Approved
0.6994	Remote Similarity	NPD6386	Approved
0.6988	Remote Similarity	NPD3749	Approved
0.6981	Remote Similarity	NPD1511	Approved
0.6977	Remote Similarity	NPD7472	Approved
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD943	Approved
0.697	Remote Similarity	NPD5402	Approved
0.6968	Remote Similarity	NPD5408	Approved
0.6968	Remote Similarity	NPD5406	Approved
0.6968	Remote Similarity	NPD5405	Approved
0.6968	Remote Similarity	NPD5404	Approved
0.6959	Remote Similarity	NPD2797	Approved
0.6959	Remote Similarity	NPD1203	Approved
0.6957	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3268	Approved
0.695	Remote Similarity	NPD2629	Approved
0.6946	Remote Similarity	NPD6234	Discontinued
0.6946	Remote Similarity	NPD919	Approved
0.6944	Remote Similarity	NPD5691	Approved
0.6944	Remote Similarity	NPD9268	Approved
0.6937	Remote Similarity	NPD5401	Approved
0.6936	Remote Similarity	NPD5953	Discontinued
0.6934	Remote Similarity	NPD1358	Approved
0.6923	Remote Similarity	NPD5711	Approved
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD5710	Approved
0.6918	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7239	Suspended
0.6913	Remote Similarity	NPD2798	Approved
0.6911	Remote Similarity	NPD7930	Approved
0.6909	Remote Similarity	NPD1465	Phase 2
0.6908	Remote Similarity	NPD4062	Phase 3
0.6903	Remote Similarity	NPD3748	Approved
0.6897	Remote Similarity	NPD7251	Discontinued
0.6897	Remote Similarity	NPD17	Approved
0.6897	Remote Similarity	NPD1778	Approved
0.6894	Remote Similarity	NPD1512	Approved
0.6894	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1283	Approved
0.6892	Remote Similarity	NPD1876	Approved
0.6884	Remote Similarity	NPD74	Approved
0.6884	Remote Similarity	NPD2182	Approved
0.6884	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9266	Approved
0.6871	Remote Similarity	NPD3972	Approved
0.6867	Remote Similarity	NPD2861	Phase 2
0.6867	Remote Similarity	NPD5353	Approved
0.6864	Remote Similarity	NPD7199	Phase 2
0.6864	Remote Similarity	NPD6959	Discontinued
0.6863	Remote Similarity	NPD2979	Phase 3
0.6861	Remote Similarity	NPD3134	Approved
0.686	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4476	Approved
0.6859	Remote Similarity	NPD4477	Approved
0.6859	Remote Similarity	NPD2438	Suspended
0.6857	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7808	Phase 3
0.6855	Remote Similarity	NPD2309	Approved
0.6849	Remote Similarity	NPD3496	Discontinued
0.6848	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD6797	Phase 2
0.6839	Remote Similarity	NPD3823	Discontinued
0.6835	Remote Similarity	NPD2067	Discontinued
0.6832	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4965	Approved
0.6826	Remote Similarity	NPD4967	Phase 2
0.6826	Remote Similarity	NPD4966	Approved
0.6824	Remote Similarity	NPD7229	Phase 3
0.6815	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2353	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