NPASS Compound

Structure

NPC471995 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 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 2.5981 1.5000 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 1.7321 1.0000 0.0000 C 0 0 1 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 15 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 23 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 14 1 0 0 0 0 13 18 1 1 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 18 1 1 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 2 1 1 0 0 0 19 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.17
Volume:	327.569
LogP:	2.256
LogD:	2.552
LogS:	-4.114
# Rotatable Bonds:	1
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	4.708
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.069
MDCK Permeability:	8.31102988740895e-06
Pgp-inhibitor:	0.02
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.218
Plasma Protein Binding (PPB):	93.03923797607422%
Volume Distribution (VD):	0.928
Pgp-substrate:	5.455182075500488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.716
CYP2C19-inhibitor:	0.275
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	15.451
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.081
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC471995

Natural Product ID:	NPC471995
*Common Name:**	VNWCNJGGBYIPDH-KRDRHDLTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VNWCNJGGBYIPDH-KRDRHDLTSA-N
Standard InCHI:	InChI=1S/C19H24O4/c1-11-13-5-6-19(10-20)14-9-23-8-12(14)3-4-16(19)18(13,2)7-15(21)17(11)22/h8-9,13,16,20,22H,3-7,10H2,1-2H3/t13-,16+,18-,19+/m0/s1
SMILES:	CC1=C(C(=O)CC2(C1CCC3(C2CCC4=COC=C43)CO)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3315156
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane diterpenoids

*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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	<	50.0	%	PMID[541643]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	ED50	=	50.0	uM	PMID[541643]

☑ 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 NPC471995 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	269
0.1-0.2	1233
0.2-0.3	2956
0.3-0.4	6483
0.4-0.5	12798
0.5-0.6	10508
0.6-0.7	7662
0.7-0.8	682
0.8-0.85	81
0.85-0.9	21
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9538	High Similarity	NPC471996
0.912	High Similarity	NPC272899
0.8992	High Similarity	NPC120836
0.8992	High Similarity	NPC223063
0.8939	High Similarity	NPC471998
0.8881	High Similarity	NPC4764
0.8828	High Similarity	NPC303010
0.8768	High Similarity	NPC243577
0.875	High Similarity	NPC130275
0.8682	High Similarity	NPC230979
0.864	High Similarity	NPC212918
0.8615	High Similarity	NPC23086
0.8613	High Similarity	NPC90953
0.8593	High Similarity	NPC158525
0.8571	High Similarity	NPC89133
0.8571	High Similarity	NPC61788
0.8561	High Similarity	NPC20578
0.8561	High Similarity	NPC62103
0.8551	High Similarity	NPC90296
0.8551	High Similarity	NPC67003
0.8529	High Similarity	NPC46896
0.8511	High Similarity	NPC41182
0.85	High Similarity	NPC103134
0.8485	Intermediate Similarity	NPC26532
0.8485	Intermediate Similarity	NPC329707
0.8467	Intermediate Similarity	NPC310043
0.845	Intermediate Similarity	NPC36255
0.8429	Intermediate Similarity	NPC473152
0.8414	Intermediate Similarity	NPC272590
0.8409	Intermediate Similarity	NPC246392
0.8394	Intermediate Similarity	NPC214572
0.8392	Intermediate Similarity	NPC471174
0.8392	Intermediate Similarity	NPC250228
0.838	Intermediate Similarity	NPC185456
0.8369	Intermediate Similarity	NPC64568
0.8367	Intermediate Similarity	NPC472785
0.8356	Intermediate Similarity	NPC246164
0.8356	Intermediate Similarity	NPC475777
0.8346	Intermediate Similarity	NPC112706
0.8346	Intermediate Similarity	NPC207294
0.8333	Intermediate Similarity	NPC138139
0.8333	Intermediate Similarity	NPC46536
0.8321	Intermediate Similarity	NPC83115
0.831	Intermediate Similarity	NPC251865
0.831	Intermediate Similarity	NPC476944
0.8309	Intermediate Similarity	NPC471006
0.8309	Intermediate Similarity	NPC218838
0.8308	Intermediate Similarity	NPC477967
0.8299	Intermediate Similarity	NPC178932
0.8298	Intermediate Similarity	NPC263337
0.8298	Intermediate Similarity	NPC121158
0.8288	Intermediate Similarity	NPC472787
0.8284	Intermediate Similarity	NPC198904
0.8276	Intermediate Similarity	NPC470998
0.8273	Intermediate Similarity	NPC476943
0.8271	Intermediate Similarity	NPC83178
0.8271	Intermediate Similarity	NPC290955
0.8264	Intermediate Similarity	NPC302987
0.8264	Intermediate Similarity	NPC216755
0.8258	Intermediate Similarity	NPC179354
0.8252	Intermediate Similarity	NPC5676
0.8243	Intermediate Similarity	NPC469336
0.8243	Intermediate Similarity	NPC35000
0.8243	Intermediate Similarity	NPC75310
0.8243	Intermediate Similarity	NPC281258
0.8243	Intermediate Similarity	NPC92979
0.8239	Intermediate Similarity	NPC267632
0.8231	Intermediate Similarity	NPC469503
0.8231	Intermediate Similarity	NPC97566
0.8227	Intermediate Similarity	NPC205765
0.8222	Intermediate Similarity	NPC476925
0.8219	Intermediate Similarity	NPC470997
0.8219	Intermediate Similarity	NPC196846
0.8212	Intermediate Similarity	NPC5079
0.8212	Intermediate Similarity	NPC69028
0.8209	Intermediate Similarity	NPC477123
0.8209	Intermediate Similarity	NPC477040
0.8209	Intermediate Similarity	NPC476917
0.8209	Intermediate Similarity	NPC477966
0.8209	Intermediate Similarity	NPC327527
0.8207	Intermediate Similarity	NPC476941
0.8207	Intermediate Similarity	NPC476942
0.8201	Intermediate Similarity	NPC310830
0.8195	Intermediate Similarity	NPC74612
0.8194	Intermediate Similarity	NPC97904
0.8188	Intermediate Similarity	NPC476947
0.8182	Intermediate Similarity	NPC178382
0.8176	Intermediate Similarity	NPC30222
0.8169	Intermediate Similarity	NPC52412
0.8158	Intermediate Similarity	NPC51568
0.8158	Intermediate Similarity	NPC234660
0.8156	Intermediate Similarity	NPC148374
0.8156	Intermediate Similarity	NPC18904
0.8151	Intermediate Similarity	NPC195325
0.8151	Intermediate Similarity	NPC211625
0.8151	Intermediate Similarity	NPC234494
0.8151	Intermediate Similarity	NPC472654
0.8146	Intermediate Similarity	NPC477402
0.8143	Intermediate Similarity	NPC220094
0.814	Intermediate Similarity	NPC243704
0.8138	Intermediate Similarity	NPC476938
0.8138	Intermediate Similarity	NPC476937
0.8133	Intermediate Similarity	NPC249021
0.8121	Intermediate Similarity	NPC44675
0.8121	Intermediate Similarity	NPC472786
0.8121	Intermediate Similarity	NPC214541
0.8121	Intermediate Similarity	NPC296807
0.8121	Intermediate Similarity	NPC141538
0.8121	Intermediate Similarity	NPC155939
0.8112	Intermediate Similarity	NPC476946
0.8108	Intermediate Similarity	NPC33938
0.8108	Intermediate Similarity	NPC470996
0.8108	Intermediate Similarity	NPC44577
0.8108	Intermediate Similarity	NPC75906
0.8106	Intermediate Similarity	NPC16922
0.8105	Intermediate Similarity	NPC276551
0.8102	Intermediate Similarity	NPC471817
0.8102	Intermediate Similarity	NPC473982
0.8085	Intermediate Similarity	NPC202260
0.8082	Intermediate Similarity	NPC471007
0.8079	Intermediate Similarity	NPC475967
0.8079	Intermediate Similarity	NPC477403
0.8074	Intermediate Similarity	NPC279877
0.8074	Intermediate Similarity	NPC477039
0.8071	Intermediate Similarity	NPC42400
0.8069	Intermediate Similarity	NPC470999
0.8069	Intermediate Similarity	NPC262198
0.8069	Intermediate Similarity	NPC346
0.8067	Intermediate Similarity	NPC469485
0.8056	Intermediate Similarity	NPC142113
0.8054	Intermediate Similarity	NPC57998
0.8054	Intermediate Similarity	NPC114880
0.8052	Intermediate Similarity	NPC470875
0.8043	Intermediate Similarity	NPC293253
0.8039	Intermediate Similarity	NPC663
0.8039	Intermediate Similarity	NPC292389
0.8039	Intermediate Similarity	NPC477405
0.8039	Intermediate Similarity	NPC224394
0.8039	Intermediate Similarity	NPC469338
0.8028	Intermediate Similarity	NPC61157
0.8028	Intermediate Similarity	NPC473681
0.8028	Intermediate Similarity	NPC218204
0.8028	Intermediate Similarity	NPC56197
0.8027	Intermediate Similarity	NPC69647
0.8027	Intermediate Similarity	NPC125182
0.8026	Intermediate Similarity	NPC335761
0.8026	Intermediate Similarity	NPC25255
0.8015	Intermediate Similarity	NPC208389
0.8014	Intermediate Similarity	NPC10088
0.8014	Intermediate Similarity	NPC255414
0.8013	Intermediate Similarity	NPC45101
0.8013	Intermediate Similarity	NPC173544
0.8013	Intermediate Similarity	NPC304692
0.8013	Intermediate Similarity	NPC261597
0.8013	Intermediate Similarity	NPC472772
0.8	Intermediate Similarity	NPC264943
0.8	Intermediate Similarity	NPC146872
0.7987	Intermediate Similarity	NPC476858
0.7987	Intermediate Similarity	NPC294511
0.7987	Intermediate Similarity	NPC121615
0.7987	Intermediate Similarity	NPC476857
0.7987	Intermediate Similarity	NPC123088
0.7987	Intermediate Similarity	NPC470940
0.7987	Intermediate Similarity	NPC469849
0.7987	Intermediate Similarity	NPC476856
0.7974	Intermediate Similarity	NPC263432
0.7974	Intermediate Similarity	NPC193798
0.7974	Intermediate Similarity	NPC82851
0.7974	Intermediate Similarity	NPC329938
0.7973	Intermediate Similarity	NPC159927
0.7973	Intermediate Similarity	NPC469335
0.7973	Intermediate Similarity	NPC228842
0.7973	Intermediate Similarity	NPC46551
0.7973	Intermediate Similarity	NPC212257
0.7961	Intermediate Similarity	NPC307383
0.7961	Intermediate Similarity	NPC474611
0.7961	Intermediate Similarity	NPC116639
0.7961	Intermediate Similarity	NPC262872
0.7949	Intermediate Similarity	NPC471397
0.7947	Intermediate Similarity	NPC104736
0.7947	Intermediate Similarity	NPC41880
0.7947	Intermediate Similarity	NPC60973
0.7947	Intermediate Similarity	NPC209364
0.7945	Intermediate Similarity	NPC62799
0.7945	Intermediate Similarity	NPC471292
0.7945	Intermediate Similarity	NPC276676
0.7935	Intermediate Similarity	NPC475779
0.7935	Intermediate Similarity	NPC23387
0.7933	Intermediate Similarity	NPC282445
0.7931	Intermediate Similarity	NPC137295
0.7931	Intermediate Similarity	NPC199044
0.7931	Intermediate Similarity	NPC238843
0.7929	Intermediate Similarity	NPC92941
0.7922	Intermediate Similarity	NPC302369
0.7922	Intermediate Similarity	NPC134254
0.7922	Intermediate Similarity	NPC39986
0.7914	Intermediate Similarity	NPC470740
0.7914	Intermediate Similarity	NPC214097
0.791	Intermediate Similarity	NPC477038
0.791	Intermediate Similarity	NPC477965

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 NPC471995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	979
0.2-0.3	1981
0.3-0.4	2789
0.4-0.5	2027
0.5-0.6	923
0.6-0.7	197
0.7-0.8	9
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
0.8	Intermediate Similarity	NPD5761	Phase 2
0.8	Intermediate Similarity	NPD5760	Phase 2
0.7586	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6765	Approved
0.7485	Intermediate Similarity	NPD6764	Approved
0.747	Intermediate Similarity	NPD8434	Phase 2
0.7452	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6785	Approved
0.7305	Intermediate Similarity	NPD6784	Approved
0.7226	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD2800	Approved
0.7114	Intermediate Similarity	NPD1471	Phase 3
0.7078	Intermediate Similarity	NPD6273	Approved
0.7013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2346	Discontinued
0.6918	Remote Similarity	NPD2313	Discontinued
0.6908	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2344	Approved
0.6867	Remote Similarity	NPD2799	Discontinued
0.6835	Remote Similarity	NPD3226	Approved
0.6831	Remote Similarity	NPD3972	Approved
0.6821	Remote Similarity	NPD6100	Approved
0.6821	Remote Similarity	NPD6099	Approved
0.6795	Remote Similarity	NPD2534	Approved
0.6795	Remote Similarity	NPD2532	Approved
0.6795	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2533	Approved
0.6792	Remote Similarity	NPD6599	Discontinued
0.6774	Remote Similarity	NPD7236	Approved
0.6753	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1608	Approved
0.671	Remote Similarity	NPD2309	Approved
0.6709	Remote Similarity	NPD920	Approved
0.669	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD3750	Approved
0.6645	Remote Similarity	NPD7003	Approved
0.6644	Remote Similarity	NPD2798	Approved
0.6644	Remote Similarity	NPD8032	Phase 2
0.6626	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7458	Discontinued
0.6623	Remote Similarity	NPD6651	Approved
0.6622	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1876	Approved
0.6601	Remote Similarity	NPD2796	Approved
0.66	Remote Similarity	NPD4140	Approved
0.6594	Remote Similarity	NPD1241	Discontinued
0.6585	Remote Similarity	NPD3882	Suspended
0.6582	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3764	Approved
0.6577	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2797	Approved
0.6566	Remote Similarity	NPD5494	Approved
0.6564	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7239	Suspended
0.6558	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3749	Approved
0.6545	Remote Similarity	NPD7075	Discontinued
0.6536	Remote Similarity	NPD3748	Approved
0.6528	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6959	Discontinued
0.6527	Remote Similarity	NPD1247	Approved
0.6527	Remote Similarity	NPD8127	Discontinued
0.6519	Remote Similarity	NPD6799	Approved
0.6516	Remote Similarity	NPD1549	Phase 2
0.6509	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD17	Approved
0.6503	Remote Similarity	NPD6801	Discontinued
0.6503	Remote Similarity	NPD1778	Approved
0.6494	Remote Similarity	NPD1551	Phase 2
0.6481	Remote Similarity	NPD4380	Phase 2
0.6481	Remote Similarity	NPD7028	Phase 2
0.6478	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6798	Discontinued
0.6463	Remote Similarity	NPD3267	Approved
0.6463	Remote Similarity	NPD3266	Approved
0.6458	Remote Similarity	NPD8404	Phase 2
0.6456	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5762	Approved
0.6452	Remote Similarity	NPD5763	Approved
0.6449	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5735	Approved
0.6442	Remote Similarity	NPD7411	Suspended
0.6434	Remote Similarity	NPD5585	Approved
0.6433	Remote Similarity	NPD4110	Phase 3
0.6433	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1510	Phase 2
0.6429	Remote Similarity	NPD7033	Discontinued
0.6429	Remote Similarity	NPD4308	Phase 3
0.6424	Remote Similarity	NPD6233	Phase 2
0.6424	Remote Similarity	NPD3817	Phase 2
0.6424	Remote Similarity	NPD5402	Approved
0.6419	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6166	Phase 2
0.6407	Remote Similarity	NPD919	Approved
0.6402	Remote Similarity	NPD1934	Approved
0.6402	Remote Similarity	NPD37	Approved
0.64	Remote Similarity	NPD7095	Approved
0.6398	Remote Similarity	NPD5403	Approved
0.6395	Remote Similarity	NPD5844	Phase 1
0.6395	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1283	Approved
0.6389	Remote Similarity	NPD2932	Approved
0.6386	Remote Similarity	NPD4966	Approved
0.6386	Remote Similarity	NPD4965	Approved
0.6386	Remote Similarity	NPD4967	Phase 2
0.6382	Remote Similarity	NPD2979	Phase 3
0.6378	Remote Similarity	NPD3057	Approved
0.6375	Remote Similarity	NPD5401	Approved
0.6369	Remote Similarity	NPD1243	Approved
0.6364	Remote Similarity	NPD2801	Approved
0.6358	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3926	Phase 2
0.6347	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3818	Discontinued
0.6337	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD1512	Approved
0.6333	Remote Similarity	NPD6832	Phase 2
0.6329	Remote Similarity	NPD8166	Discontinued
0.6328	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5327	Phase 3
0.6319	Remote Similarity	NPD1651	Approved
0.6312	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD5647	Approved
0.6307	Remote Similarity	NPD8313	Approved
0.6307	Remote Similarity	NPD8312	Approved
0.6306	Remote Similarity	NPD4534	Discontinued
0.6306	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD2424	Discontinued
0.6303	Remote Similarity	NPD6844	Discontinued
0.6303	Remote Similarity	NPD6280	Approved
0.6303	Remote Similarity	NPD6279	Approved
0.6299	Remote Similarity	NPD1607	Approved
0.6294	Remote Similarity	NPD9092	Discovery
0.6294	Remote Similarity	NPD5710	Approved
0.6294	Remote Similarity	NPD5711	Approved
0.6294	Remote Similarity	NPD7229	Phase 3
0.629	Remote Similarity	NPD3533	Approved
0.629	Remote Similarity	NPD2972	Approved
0.6289	Remote Similarity	NPD3887	Approved
0.6289	Remote Similarity	NPD2354	Approved
0.6287	Remote Similarity	NPD7768	Phase 2
0.6287	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7058	Phase 2
0.6287	Remote Similarity	NPD7057	Phase 3
0.6284	Remote Similarity	NPD8651	Approved
0.6284	Remote Similarity	NPD6696	Suspended
0.6282	Remote Similarity	NPD2935	Discontinued
0.6282	Remote Similarity	NPD4476	Approved
0.6282	Remote Similarity	NPD4477	Approved
0.6279	Remote Similarity	NPD7473	Discontinued
0.6276	Remote Similarity	NPD3019	Approved
0.6275	Remote Similarity	NPD1240	Approved
0.6275	Remote Similarity	NPD4060	Phase 1
0.6275	Remote Similarity	NPD4307	Phase 2
0.6268	Remote Similarity	NPD7157	Approved
0.6259	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7985	Registered
0.625	Remote Similarity	NPD1894	Discontinued
0.6243	Remote Similarity	NPD7799	Discontinued
0.6243	Remote Similarity	NPD7177	Discontinued
0.6235	Remote Similarity	NPD5049	Phase 3
0.6234	Remote Similarity	NPD4622	Approved
0.6234	Remote Similarity	NPD4618	Approved
0.6229	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD2296	Approved
0.6226	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD2403	Approved
0.6221	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2651	Approved
0.622	Remote Similarity	NPD2649	Approved
0.6216	Remote Similarity	NPD4359	Approved
0.6213	Remote Similarity	NPD6234	Discontinued
0.6211	Remote Similarity	NPD1511	Approved
0.6209	Remote Similarity	NPD4062	Phase 3
0.6205	Remote Similarity	NPD7577	Discontinued
0.6203	Remote Similarity	NPD5958	Discontinued
0.6203	Remote Similarity	NPD2491	Approved
0.6199	Remote Similarity	NPD6232	Discontinued
0.6197	Remote Similarity	NPD2629	Approved
0.6196	Remote Similarity	NPD3873	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