NPASS Compound

Structure

NPC471996 OpenBabel07101718182D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 0.8660 -0.5000 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 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 0.0000 1.0000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 17 1 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 24 1 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 21 2 0 0 0 0 15 17 1 1 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 1 0 0 0 18 10 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	336.36
LogP:	1.113
LogD:	1.245
LogS:	-3.425
# Rotatable Bonds:	1
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	4.923
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:	-5.001
MDCK Permeability:	1.0333396858186461e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.59
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.726
Plasma Protein Binding (PPB):	87.92092895507812%
Volume Distribution (VD):	0.817
Pgp-substrate:	11.441777229309082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.368
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.393
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	10.09
Half-life (T1/2):	0.419

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.105
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC471996

Natural Product ID:	NPC471996
*Common Name:**	YJYCGDAWLMWZRS-WUDVTJOCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YJYCGDAWLMWZRS-WUDVTJOCSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-11-16(22)14(21)7-17(2)15-4-3-12-8-24-9-13(12)18(15,10-20)5-6-19(11,17)23/h8-9,15,20,22-23H,3-7,10H2,1-2H3/t15-,17-,18-,19?/m1/s1
SMILES:	CC1=C(C(=O)CC2(C1(CCC3(C2CCC4=COC=C43)CO)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3315157
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
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2
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	IC50	=	34400.0	nM	PMID[490393]
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	CD	=	11.2	uM	PMID[490393]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	ED50	=	50.0	uM	PMID[490393]

☑ 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 NPC471996 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	292
0.1-0.2	1292
0.2-0.3	3056
0.3-0.4	5855
0.4-0.5	11534
0.5-0.6	10031
0.6-0.7	9247
0.7-0.8	1254
0.8-0.85	114
0.85-0.9	16
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9538	High Similarity	NPC471995
0.9065	High Similarity	NPC243577
0.9044	High Similarity	NPC4764
0.8857	High Similarity	NPC62103
0.8857	High Similarity	NPC20578
0.8849	High Similarity	NPC67003
0.8714	High Similarity	NPC90296
0.8702	High Similarity	NPC272899
0.8696	High Similarity	NPC46896
0.8671	High Similarity	NPC41182
0.8662	High Similarity	NPC64568
0.8662	High Similarity	NPC103134
0.8649	High Similarity	NPC472785
0.8633	High Similarity	NPC310043
0.8623	High Similarity	NPC158525
0.8611	High Similarity	NPC97904
0.8603	High Similarity	NPC61788
0.8601	High Similarity	NPC251865
0.8593	High Similarity	NPC223063
0.8593	High Similarity	NPC120836
0.8592	High Similarity	NPC121158
0.8592	High Similarity	NPC263337
0.8562	High Similarity	NPC470998
0.8561	High Similarity	NPC214572
0.8552	High Similarity	NPC471174
0.8551	High Similarity	NPC471998
0.8542	High Similarity	NPC5676
0.8533	High Similarity	NPC249021
0.8523	High Similarity	NPC35000
0.8514	High Similarity	NPC246164
0.8514	High Similarity	NPC475777
0.8511	High Similarity	NPC90953
0.8487	Intermediate Similarity	NPC5079
0.8456	Intermediate Similarity	NPC114880
0.8456	Intermediate Similarity	NPC178932
0.8456	Intermediate Similarity	NPC30222
0.8446	Intermediate Similarity	NPC472787
0.8446	Intermediate Similarity	NPC272590
0.8435	Intermediate Similarity	NPC211625
0.8433	Intermediate Similarity	NPC303010
0.8431	Intermediate Similarity	NPC51568
0.8431	Intermediate Similarity	NPC224394
0.8431	Intermediate Similarity	NPC663
0.8431	Intermediate Similarity	NPC234660
0.8425	Intermediate Similarity	NPC216755
0.8421	Intermediate Similarity	NPC477402
0.8414	Intermediate Similarity	NPC185456
0.8411	Intermediate Similarity	NPC261597
0.8403	Intermediate Similarity	NPC476946
0.84	Intermediate Similarity	NPC214541
0.84	Intermediate Similarity	NPC44675
0.84	Intermediate Similarity	NPC92979
0.84	Intermediate Similarity	NPC469336
0.84	Intermediate Similarity	NPC472786
0.84	Intermediate Similarity	NPC75310
0.8389	Intermediate Similarity	NPC469503
0.8378	Intermediate Similarity	NPC196846
0.8377	Intermediate Similarity	NPC276551
0.8377	Intermediate Similarity	NPC470940
0.837	Intermediate Similarity	NPC23086
0.8366	Intermediate Similarity	NPC69028
0.8366	Intermediate Similarity	NPC82851
0.8366	Intermediate Similarity	NPC329938
0.8358	Intermediate Similarity	NPC130275
0.8357	Intermediate Similarity	NPC476947
0.8355	Intermediate Similarity	NPC477403
0.8355	Intermediate Similarity	NPC475967
0.8345	Intermediate Similarity	NPC218838
0.8345	Intermediate Similarity	NPC476944
0.8333	Intermediate Similarity	NPC57998
0.8333	Intermediate Similarity	NPC52412
0.8333	Intermediate Similarity	NPC282445
0.8323	Intermediate Similarity	NPC470875
0.8322	Intermediate Similarity	NPC473681
0.8322	Intermediate Similarity	NPC218204
0.8322	Intermediate Similarity	NPC61157
0.8321	Intermediate Similarity	NPC198904
0.8312	Intermediate Similarity	NPC469338
0.8312	Intermediate Similarity	NPC477405
0.8312	Intermediate Similarity	NPC292389
0.8311	Intermediate Similarity	NPC472654
0.8311	Intermediate Similarity	NPC195325
0.8311	Intermediate Similarity	NPC125182
0.8311	Intermediate Similarity	NPC69647
0.8301	Intermediate Similarity	NPC335761
0.8299	Intermediate Similarity	NPC255414
0.8299	Intermediate Similarity	NPC250228
0.8299	Intermediate Similarity	NPC302987
0.8296	Intermediate Similarity	NPC230979
0.8289	Intermediate Similarity	NPC472772
0.8289	Intermediate Similarity	NPC304692
0.8289	Intermediate Similarity	NPC36655
0.8278	Intermediate Similarity	NPC296807
0.8278	Intermediate Similarity	NPC141538
0.8278	Intermediate Similarity	NPC155939
0.8267	Intermediate Similarity	NPC75906
0.8267	Intermediate Similarity	NPC33938
0.8267	Intermediate Similarity	NPC470996
0.8258	Intermediate Similarity	NPC476857
0.8258	Intermediate Similarity	NPC469849
0.8258	Intermediate Similarity	NPC476856
0.8258	Intermediate Similarity	NPC476858
0.8255	Intermediate Similarity	NPC228842
0.8255	Intermediate Similarity	NPC470997
0.8255	Intermediate Similarity	NPC212257
0.8248	Intermediate Similarity	NPC329707
0.8247	Intermediate Similarity	NPC193798
0.8244	Intermediate Similarity	NPC212918
0.8243	Intermediate Similarity	NPC471007
0.8231	Intermediate Similarity	NPC470999
0.8231	Intermediate Similarity	NPC346
0.8224	Intermediate Similarity	NPC469485
0.8224	Intermediate Similarity	NPC41880
0.8224	Intermediate Similarity	NPC104736
0.8224	Intermediate Similarity	NPC209364
0.8222	Intermediate Similarity	NPC178382
0.8217	Intermediate Similarity	NPC471397
0.8214	Intermediate Similarity	NPC293253
0.8207	Intermediate Similarity	NPC473152
0.8205	Intermediate Similarity	NPC23387
0.8201	Intermediate Similarity	NPC89133
0.8194	Intermediate Similarity	NPC18904
0.8194	Intermediate Similarity	NPC134254
0.8194	Intermediate Similarity	NPC39986
0.8194	Intermediate Similarity	NPC302369
0.8188	Intermediate Similarity	NPC234494
0.8182	Intermediate Similarity	NPC25255
0.8182	Intermediate Similarity	NPC472653
0.817	Intermediate Similarity	NPC45101
0.817	Intermediate Similarity	NPC173544
0.817	Intermediate Similarity	NPC187149
0.817	Intermediate Similarity	NPC194499
0.817	Intermediate Similarity	NPC286722
0.817	Intermediate Similarity	NPC470118
0.8158	Intermediate Similarity	NPC264943
0.8153	Intermediate Similarity	NPC472774
0.8153	Intermediate Similarity	NPC476853
0.8153	Intermediate Similarity	NPC472282
0.8153	Intermediate Similarity	NPC476861
0.8153	Intermediate Similarity	NPC472775
0.8153	Intermediate Similarity	NPC173516
0.8153	Intermediate Similarity	NPC476850
0.8146	Intermediate Similarity	NPC44577
0.8146	Intermediate Similarity	NPC268905
0.8146	Intermediate Similarity	NPC294511
0.8146	Intermediate Similarity	NPC121615
0.8141	Intermediate Similarity	NPC476860
0.8141	Intermediate Similarity	NPC123088
0.8133	Intermediate Similarity	NPC196864
0.8133	Intermediate Similarity	NPC477404
0.8133	Intermediate Similarity	NPC469335
0.8133	Intermediate Similarity	NPC159927
0.8129	Intermediate Similarity	NPC200782
0.8129	Intermediate Similarity	NPC290400
0.8129	Intermediate Similarity	NPC263432
0.8129	Intermediate Similarity	NPC472771
0.8129	Intermediate Similarity	NPC149896
0.8129	Intermediate Similarity	NPC117986
0.8129	Intermediate Similarity	NPC96443
0.8125	Intermediate Similarity	NPC202260
0.8121	Intermediate Similarity	NPC19747
0.8117	Intermediate Similarity	NPC474611
0.8117	Intermediate Similarity	NPC472823
0.8117	Intermediate Similarity	NPC473473
0.8117	Intermediate Similarity	NPC307383
0.8117	Intermediate Similarity	NPC475295
0.8116	Intermediate Similarity	NPC279877
0.8116	Intermediate Similarity	NPC26532
0.8116	Intermediate Similarity	NPC112706
0.8116	Intermediate Similarity	NPC207294
0.8108	Intermediate Similarity	NPC62799
0.8105	Intermediate Similarity	NPC60973
0.8105	Intermediate Similarity	NPC107646
0.8089	Intermediate Similarity	NPC475779
0.8089	Intermediate Similarity	NPC478178
0.8077	Intermediate Similarity	NPC472773
0.8077	Intermediate Similarity	NPC283209
0.8074	Intermediate Similarity	NPC36255
0.8069	Intermediate Similarity	NPC56197
0.8067	Intermediate Similarity	NPC471001
0.8065	Intermediate Similarity	NPC287559
0.8065	Intermediate Similarity	NPC470789
0.8054	Intermediate Similarity	NPC221809
0.8052	Intermediate Similarity	NPC195954
0.8052	Intermediate Similarity	NPC197137
0.8052	Intermediate Similarity	NPC88007
0.8052	Intermediate Similarity	NPC299038
0.8052	Intermediate Similarity	NPC472283
0.805	Intermediate Similarity	NPC470995
0.8043	Intermediate Similarity	NPC290955
0.8043	Intermediate Similarity	NPC246392
0.8039	Intermediate Similarity	NPC469850
0.8038	Intermediate Similarity	NPC478179
0.8038	Intermediate Similarity	NPC472651
0.8038	Intermediate Similarity	NPC472784
0.8027	Intermediate Similarity	NPC205071
0.8026	Intermediate Similarity	NPC472672
0.8026	Intermediate Similarity	NPC476940
0.8026	Intermediate Similarity	NPC476939
0.8025	Intermediate Similarity	NPC271657

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 NPC471996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	1021
0.2-0.3	2085
0.3-0.4	2683
0.4-0.5	1926
0.5-0.6	915
0.6-0.7	249
0.7-0.8	14
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
0.84	Intermediate Similarity	NPD5760	Phase 2
0.84	Intermediate Similarity	NPD5761	Phase 2
0.7831	Intermediate Similarity	NPD8434	Phase 2
0.7636	Intermediate Similarity	NPD6765	Approved
0.7636	Intermediate Similarity	NPD6764	Approved
0.761	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6785	Approved
0.7456	Intermediate Similarity	NPD6784	Approved
0.74	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2800	Approved
0.7255	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1471	Phase 3
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2532	Approved
0.707	Intermediate Similarity	NPD2534	Approved
0.707	Intermediate Similarity	NPD2533	Approved
0.7032	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD3226	Approved
0.6962	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2344	Approved
0.6948	Remote Similarity	NPD2346	Discontinued
0.6943	Remote Similarity	NPD7236	Approved
0.6923	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6559	Discontinued
0.6852	Remote Similarity	NPD6599	Discontinued
0.6848	Remote Similarity	NPD3882	Suspended
0.6829	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7819	Suspended
0.6818	Remote Similarity	NPD2799	Discontinued
0.6815	Remote Similarity	NPD3750	Approved
0.6807	Remote Similarity	NPD3749	Approved
0.6797	Remote Similarity	NPD6651	Approved
0.6788	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6959	Discontinued
0.6772	Remote Similarity	NPD2309	Approved
0.6771	Remote Similarity	NPD8404	Phase 2
0.677	Remote Similarity	NPD920	Approved
0.6755	Remote Similarity	NPD3764	Approved
0.6755	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2313	Discontinued
0.675	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6005	Phase 3
0.6731	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6004	Phase 3
0.6731	Remote Similarity	NPD6002	Phase 3
0.6728	Remote Similarity	NPD7239	Suspended
0.6727	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5494	Approved
0.6709	Remote Similarity	NPD7003	Approved
0.6707	Remote Similarity	NPD7075	Discontinued
0.6688	Remote Similarity	NPD1549	Phase 2
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7458	Discontinued
0.6686	Remote Similarity	NPD8127	Discontinued
0.6686	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4965	Approved
0.6647	Remote Similarity	NPD5844	Phase 1
0.6647	Remote Similarity	NPD4966	Approved
0.6647	Remote Similarity	NPD4967	Phase 2
0.6646	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4380	Phase 2
0.6645	Remote Similarity	NPD3268	Approved
0.6645	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2801	Approved
0.6623	Remote Similarity	NPD6355	Discontinued
0.6613	Remote Similarity	NPD3057	Approved
0.6606	Remote Similarity	NPD7411	Suspended
0.6605	Remote Similarity	NPD1512	Approved
0.6603	Remote Similarity	NPD7033	Discontinued
0.6603	Remote Similarity	NPD1510	Phase 2
0.6603	Remote Similarity	NPD3748	Approved
0.6601	Remote Similarity	NPD8032	Phase 2
0.659	Remote Similarity	NPD3818	Discontinued
0.6587	Remote Similarity	NPD5402	Approved
0.6587	Remote Similarity	NPD3817	Phase 2
0.6584	Remote Similarity	NPD6799	Approved
0.6582	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6696	Suspended
0.657	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD919	Approved
0.6561	Remote Similarity	NPD1551	Phase 2
0.6558	Remote Similarity	NPD4140	Approved
0.6552	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5710	Approved
0.655	Remote Similarity	NPD5711	Approved
0.6548	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7028	Phase 2
0.6533	Remote Similarity	NPD2797	Approved
0.6532	Remote Similarity	NPD7473	Discontinued
0.6524	Remote Similarity	NPD2972	Approved
0.6524	Remote Similarity	NPD3533	Approved
0.6522	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5762	Approved
0.6519	Remote Similarity	NPD5763	Approved
0.6512	Remote Similarity	NPD3926	Phase 2
0.6509	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4308	Phase 3
0.6497	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3751	Discontinued
0.6494	Remote Similarity	NPD7799	Discontinued
0.649	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2798	Approved
0.6484	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1511	Approved
0.6481	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1607	Approved
0.6471	Remote Similarity	NPD7095	Approved
0.6471	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6234	Discontinued
0.6467	Remote Similarity	NPD1876	Approved
0.6463	Remote Similarity	NPD2932	Approved
0.6463	Remote Similarity	NPD1778	Approved
0.6463	Remote Similarity	NPD5403	Approved
0.6463	Remote Similarity	NPD17	Approved
0.6461	Remote Similarity	NPD8313	Approved
0.6461	Remote Similarity	NPD8312	Approved
0.6456	Remote Similarity	NPD2935	Discontinued
0.6453	Remote Similarity	NPD6232	Discontinued
0.6453	Remote Similarity	NPD7229	Phase 3
0.6452	Remote Similarity	NPD1240	Approved
0.6452	Remote Similarity	NPD4060	Phase 1
0.645	Remote Similarity	NPD7768	Phase 2
0.645	Remote Similarity	NPD7058	Phase 2
0.645	Remote Similarity	NPD7057	Phase 3
0.6447	Remote Similarity	NPD2861	Phase 2
0.6442	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1243	Approved
0.6436	Remote Similarity	NPD2491	Approved
0.6434	Remote Similarity	NPD1241	Discontinued
0.6429	Remote Similarity	NPD6798	Discontinued
0.6429	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5124	Phase 1
0.641	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5735	Approved
0.64	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4749	Approved
0.64	Remote Similarity	NPD7177	Discontinued
0.6398	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4110	Phase 3
0.6398	Remote Similarity	NPD8166	Discontinued
0.6384	Remote Similarity	NPD6797	Phase 2
0.6382	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD2403	Approved
0.6379	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2424	Discontinued
0.6364	Remote Similarity	NPD4665	Approved
0.6364	Remote Similarity	NPD4111	Phase 1
0.6358	Remote Similarity	NPD1283	Approved
0.6358	Remote Similarity	NPD8651	Approved
0.6358	Remote Similarity	NPD3787	Discontinued
0.6354	Remote Similarity	NPD8150	Discontinued
0.6351	Remote Similarity	NPD3019	Approved
0.6349	Remote Similarity	NPD3448	Approved
0.6348	Remote Similarity	NPD7251	Discontinued
0.6348	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2979	Phase 3
0.6341	Remote Similarity	NPD5401	Approved
0.634	Remote Similarity	NPD5676	Approved
0.6333	Remote Similarity	NPD8407	Phase 2
0.633	Remote Similarity	NPD4107	Approved
0.6328	Remote Similarity	NPD7074	Phase 3
0.6323	Remote Similarity	NPD7985	Registered
0.6323	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3300	Phase 2
0.6316	Remote Similarity	NPD3267	Approved
0.6316	Remote Similarity	NPD3266	Approved
0.6316	Remote Similarity	NPD1470	Approved
0.6313	Remote Similarity	NPD7808	Phase 3
0.6313	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7228	Approved
0.6303	Remote Similarity	NPD5049	Phase 3
0.6301	Remote Similarity	NPD7199	Phase 2
0.6299	Remote Similarity	NPD4908	Phase 1
0.6296	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2296	Approved
0.6291	Remote Similarity	NPD5327	Phase 3
0.6284	Remote Similarity	NPD1651	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