NPASS Compound

Structure

NPC90296 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 3.3411 -0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8768 0.3399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4643 1.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6083 -1.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3776 -2.0342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9513 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4125 -1.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8042 -1.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4807 -1.7939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -0.6955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6083 0.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8889 -0.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 -1.3776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6083 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8042 1.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4125 -0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8042 -0.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8042 2.3214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8571 0.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7367 0.5653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7163 -0.0389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 24 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 18 20 1 6 0 0 0 19 20 1 6 0 0 0 19 22 1 0 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.174
LogD:	3.48
LogS:	-4.409
# Rotatable Bonds:	3
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.89
Synthetic Accessibility Score:	4.469
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.745
MDCK Permeability:	2.426867104077246e-05
Pgp-inhibitor:	0.455
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.686
Plasma Protein Binding (PPB):	94.81970977783203%
Volume Distribution (VD):	1.66
Pgp-substrate:	6.125248432159424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.617
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.109
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	7.055
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.662
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.155
Carcinogencity:	0.96
Eye Corrosion:	0.006
Eye Irritation:	0.018
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC90296

Natural Product ID:	NPC90296
*Common Name:**	(8R,9S,10S)-15,16-Epoxy-8Beta,9Alpha-Dihydroxylabda-5,13(16),14-Trien-7-One
IUPAC Name:	(3R,4S,4aS)-4-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one
Synonyms:
Standard InCHIKey:	QARMCHBZCFCHAP-UFYCRDLUSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-17(2)8-5-9-18(3)15(17)12-16(21)19(4,22)20(18,23)10-6-14-7-11-24-13-14/h7,11-13,22-23H,5-6,8-10H2,1-4H3/t18-,19-,20-/m0/s1
SMILES:	O=C1C=C2C(C)(C)CCC[C@@]2([C@@]([C@@]1(C)O)(O)CCc1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234606
PubChem CID:	90670467
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[469582]

☑ 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 NPC90296 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	277
0.1-0.2	1283
0.2-0.3	2937
0.3-0.4	6778
0.4-0.5	12403
0.5-0.6	8402
0.6-0.7	8523
0.7-0.8	1939
0.8-0.85	130
0.85-0.9	19
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC158525
0.9259	High Similarity	NPC46896
0.9071	High Similarity	NPC243577
0.8912	High Similarity	NPC44675
0.8912	High Similarity	NPC214541
0.8857	High Similarity	NPC67003
0.8811	High Similarity	NPC5676
0.8792	High Similarity	NPC261597
0.8792	High Similarity	NPC36655
0.8792	High Similarity	NPC187149
0.8759	High Similarity	NPC218838
0.8732	High Similarity	NPC121158
0.8732	High Similarity	NPC52412
0.8732	High Similarity	NPC263337
0.8732	High Similarity	NPC473152
0.8725	High Similarity	NPC469485
0.8714	High Similarity	NPC471996
0.8684	High Similarity	NPC469338
0.8684	High Similarity	NPC292389
0.8675	High Similarity	NPC477402
0.8667	High Similarity	NPC173544
0.8658	High Similarity	NPC264943
0.8649	High Similarity	NPC44577
0.8639	High Similarity	NPC228842
0.8633	High Similarity	NPC476947
0.8627	High Similarity	NPC470940
0.8627	High Similarity	NPC469849
0.8627	High Similarity	NPC276551
0.8618	High Similarity	NPC329938
0.8618	High Similarity	NPC69028
0.8618	High Similarity	NPC149896
0.8618	High Similarity	NPC5079
0.8613	High Similarity	NPC61788
0.8611	High Similarity	NPC251865
0.8609	High Similarity	NPC477403
0.8609	High Similarity	NPC475967
0.8571	High Similarity	NPC470875
0.8571	High Similarity	NPC125182
0.8571	High Similarity	NPC69647
0.8562	High Similarity	NPC471174
0.8562	High Similarity	NPC477405
0.8562	High Similarity	NPC234660
0.8562	High Similarity	NPC255414
0.8562	High Similarity	NPC51568
0.8553	High Similarity	NPC470789
0.8551	High Similarity	NPC471995
0.8543	High Similarity	NPC249021
0.8543	High Similarity	NPC45101
0.8542	High Similarity	NPC476946
0.8529	High Similarity	NPC26532
0.8523	High Similarity	NPC246164
0.8519	High Similarity	NPC23086
0.8516	High Similarity	NPC173516
0.8514	High Similarity	NPC196846
0.8497	Intermediate Similarity	NPC82851
0.8497	Intermediate Similarity	NPC18347
0.8483	Intermediate Similarity	NPC137295
0.8477	Intermediate Similarity	NPC209364
0.8467	Intermediate Similarity	NPC178932
0.8467	Intermediate Similarity	NPC30222
0.8467	Intermediate Similarity	NPC57998
0.8462	Intermediate Similarity	NPC148374
0.8462	Intermediate Similarity	NPC471397
0.8456	Intermediate Similarity	NPC272590
0.8456	Intermediate Similarity	NPC246392
0.8446	Intermediate Similarity	NPC470998
0.8446	Intermediate Similarity	NPC472654
0.8446	Intermediate Similarity	NPC195325
0.8442	Intermediate Similarity	NPC663
0.8442	Intermediate Similarity	NPC224394
0.8435	Intermediate Similarity	NPC216755
0.8435	Intermediate Similarity	NPC250228
0.8435	Intermediate Similarity	NPC302987
0.8431	Intermediate Similarity	NPC25255
0.8431	Intermediate Similarity	NPC335761
0.8431	Intermediate Similarity	NPC287559
0.8431	Intermediate Similarity	NPC472653
0.8421	Intermediate Similarity	NPC286722
0.8421	Intermediate Similarity	NPC299038
0.8414	Intermediate Similarity	NPC223415
0.8411	Intermediate Similarity	NPC92979
0.8411	Intermediate Similarity	NPC155939
0.8411	Intermediate Similarity	NPC141538
0.8411	Intermediate Similarity	NPC469336
0.8411	Intermediate Similarity	NPC296807
0.8411	Intermediate Similarity	NPC35000
0.84	Intermediate Similarity	NPC75906
0.84	Intermediate Similarity	NPC469503
0.84	Intermediate Similarity	NPC470996
0.84	Intermediate Similarity	NPC268905
0.84	Intermediate Similarity	NPC121615
0.84	Intermediate Similarity	NPC294511
0.8397	Intermediate Similarity	NPC472775
0.8397	Intermediate Similarity	NPC472774
0.8397	Intermediate Similarity	NPC472282
0.8394	Intermediate Similarity	NPC207294
0.8394	Intermediate Similarity	NPC112706
0.8392	Intermediate Similarity	NPC90953
0.8389	Intermediate Similarity	NPC212257
0.8387	Intermediate Similarity	NPC476860
0.8387	Intermediate Similarity	NPC476856
0.8387	Intermediate Similarity	NPC476857
0.8387	Intermediate Similarity	NPC476858
0.8387	Intermediate Similarity	NPC271657
0.8377	Intermediate Similarity	NPC18986
0.8377	Intermediate Similarity	NPC263432
0.8377	Intermediate Similarity	NPC193798
0.8367	Intermediate Similarity	NPC346
0.8367	Intermediate Similarity	NPC470999
0.8366	Intermediate Similarity	NPC307383
0.8366	Intermediate Similarity	NPC473473
0.8366	Intermediate Similarity	NPC475295
0.8356	Intermediate Similarity	NPC476944
0.8356	Intermediate Similarity	NPC86935
0.8355	Intermediate Similarity	NPC60973
0.8355	Intermediate Similarity	NPC107646
0.8345	Intermediate Similarity	NPC89133
0.8344	Intermediate Similarity	NPC282445
0.8344	Intermediate Similarity	NPC160651
0.8333	Intermediate Similarity	NPC243704
0.8333	Intermediate Similarity	NPC475779
0.8333	Intermediate Similarity	NPC478178
0.8333	Intermediate Similarity	NPC23387
0.8323	Intermediate Similarity	NPC472773
0.8323	Intermediate Similarity	NPC134254
0.8323	Intermediate Similarity	NPC39986
0.8323	Intermediate Similarity	NPC302369
0.8322	Intermediate Similarity	NPC211625
0.8322	Intermediate Similarity	NPC234494
0.8321	Intermediate Similarity	NPC83178
0.8311	Intermediate Similarity	NPC221809
0.8301	Intermediate Similarity	NPC472283
0.8301	Intermediate Similarity	NPC88007
0.8301	Intermediate Similarity	NPC194499
0.8301	Intermediate Similarity	NPC470118
0.8301	Intermediate Similarity	NPC472772
0.8301	Intermediate Similarity	NPC472778
0.8301	Intermediate Similarity	NPC472776
0.8301	Intermediate Similarity	NPC197137
0.8301	Intermediate Similarity	NPC472777
0.8301	Intermediate Similarity	NPC7059
0.8299	Intermediate Similarity	NPC185456
0.8291	Intermediate Similarity	NPC470995
0.8289	Intermediate Similarity	NPC281258
0.8286	Intermediate Similarity	NPC473344
0.8286	Intermediate Similarity	NPC471544
0.828	Intermediate Similarity	NPC478179
0.828	Intermediate Similarity	NPC472651
0.828	Intermediate Similarity	NPC476850
0.828	Intermediate Similarity	NPC476861
0.828	Intermediate Similarity	NPC476853
0.8269	Intermediate Similarity	NPC123088
0.8269	Intermediate Similarity	NPC470182
0.8267	Intermediate Similarity	NPC469335
0.8267	Intermediate Similarity	NPC196864
0.8267	Intermediate Similarity	NPC156189
0.8267	Intermediate Similarity	NPC159927
0.8267	Intermediate Similarity	NPC477404
0.8267	Intermediate Similarity	NPC470997
0.8261	Intermediate Similarity	NPC477123
0.8261	Intermediate Similarity	NPC477966
0.8258	Intermediate Similarity	NPC117986
0.8258	Intermediate Similarity	NPC211777
0.8258	Intermediate Similarity	NPC96443
0.8258	Intermediate Similarity	NPC188649
0.8258	Intermediate Similarity	NPC472771
0.8258	Intermediate Similarity	NPC200782
0.8258	Intermediate Similarity	NPC290400
0.8255	Intermediate Similarity	NPC471007
0.8252	Intermediate Similarity	NPC310830
0.825	Intermediate Similarity	NPC94763
0.825	Intermediate Similarity	NPC236004
0.8248	Intermediate Similarity	NPC46536
0.8248	Intermediate Similarity	NPC138139
0.8247	Intermediate Similarity	NPC472779
0.8247	Intermediate Similarity	NPC472823
0.8247	Intermediate Similarity	NPC262872
0.8243	Intermediate Similarity	NPC262198
0.8239	Intermediate Similarity	NPC169299
0.8239	Intermediate Similarity	NPC160818
0.8235	Intermediate Similarity	NPC263265
0.8235	Intermediate Similarity	NPC126723
0.8228	Intermediate Similarity	NPC271235
0.8228	Intermediate Similarity	NPC472652
0.8222	Intermediate Similarity	NPC477967
0.8217	Intermediate Similarity	NPC121995
0.8212	Intermediate Similarity	NPC18135
0.8207	Intermediate Similarity	NPC56197
0.8205	Intermediate Similarity	NPC288602
0.8205	Intermediate Similarity	NPC165218
0.8205	Intermediate Similarity	NPC198047
0.8205	Intermediate Similarity	NPC88841
0.8201	Intermediate Similarity	NPC59502
0.82	Intermediate Similarity	NPC470790
0.82	Intermediate Similarity	NPC470791
0.82	Intermediate Similarity	NPC471001
0.8194	Intermediate Similarity	NPC191828
0.8194	Intermediate Similarity	NPC476943
0.8194	Intermediate Similarity	NPC8389
0.8194	Intermediate Similarity	NPC236532

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 NPC90296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	924
0.2-0.3	1893
0.3-0.4	2734
0.4-0.5	2075
0.5-0.6	966
0.6-0.7	265
0.7-0.8	25
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
0.8289	Intermediate Similarity	NPD5761	Phase 2
0.8289	Intermediate Similarity	NPD5760	Phase 2
0.7952	Intermediate Similarity	NPD8434	Phase 2
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD6764	Approved
0.7651	Intermediate Similarity	NPD6765	Approved
0.7651	Intermediate Similarity	NPD1471	Phase 3
0.7628	Intermediate Similarity	NPD6599	Discontinued
0.7516	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6785	Approved
0.7471	Intermediate Similarity	NPD6784	Approved
0.7391	Intermediate Similarity	NPD3882	Suspended
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6799	Approved
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2344	Approved
0.7301	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7215	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD1247	Approved
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2800	Approved
0.719	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3972	Approved
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7124	Intermediate Similarity	NPD2796	Approved
0.7115	Intermediate Similarity	NPD2309	Approved
0.7099	Intermediate Similarity	NPD6801	Discontinued
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7044	Intermediate Similarity	NPD6273	Approved
0.7032	Intermediate Similarity	NPD1549	Phase 2
0.703	Intermediate Similarity	NPD3749	Approved
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.7019	Intermediate Similarity	NPD3226	Approved
0.7012	Intermediate Similarity	NPD3817	Phase 2
0.7007	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1934	Approved
0.6987	Remote Similarity	NPD1243	Approved
0.6981	Remote Similarity	NPD2532	Approved
0.6981	Remote Similarity	NPD2533	Approved
0.6981	Remote Similarity	NPD2534	Approved
0.6981	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4380	Phase 2
0.6968	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2346	Discontinued
0.6948	Remote Similarity	NPD1510	Phase 2
0.6946	Remote Similarity	NPD5494	Approved
0.6943	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD7411	Suspended
0.6929	Remote Similarity	NPD1241	Discontinued
0.6928	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD1608	Approved
0.6909	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1240	Approved
0.6903	Remote Similarity	NPD6099	Approved
0.6903	Remote Similarity	NPD6100	Approved
0.6903	Remote Similarity	NPD1551	Phase 2
0.6899	Remote Similarity	NPD2354	Approved
0.6882	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6166	Phase 2
0.6882	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8404	Phase 2
0.6863	Remote Similarity	NPD6355	Discontinued
0.6853	Remote Similarity	NPD9092	Discovery
0.6848	Remote Similarity	NPD2801	Approved
0.6835	Remote Similarity	NPD3750	Approved
0.6826	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7095	Approved
0.6815	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1511	Approved
0.6811	Remote Similarity	NPD3057	Approved
0.681	Remote Similarity	NPD7458	Discontinued
0.6805	Remote Similarity	NPD6959	Discontinued
0.6802	Remote Similarity	NPD3818	Discontinued
0.6802	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9494	Approved
0.6792	Remote Similarity	NPD3887	Approved
0.679	Remote Similarity	NPD5403	Approved
0.6776	Remote Similarity	NPD2313	Discontinued
0.6776	Remote Similarity	NPD3764	Approved
0.677	Remote Similarity	NPD5401	Approved
0.677	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7236	Approved
0.6735	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2798	Approved
0.6731	Remote Similarity	NPD7033	Discontinued
0.6731	Remote Similarity	NPD3748	Approved
0.672	Remote Similarity	NPD2972	Approved
0.672	Remote Similarity	NPD3533	Approved
0.6712	Remote Similarity	NPD1778	Approved
0.6712	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD17	Approved
0.6711	Remote Similarity	NPD1876	Approved
0.671	Remote Similarity	NPD6651	Approved
0.6708	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD3751	Discontinued
0.6705	Remote Similarity	NPD2163	Approved
0.669	Remote Similarity	NPD9545	Approved
0.6688	Remote Similarity	NPD2935	Discontinued
0.6687	Remote Similarity	NPD6279	Approved
0.6687	Remote Similarity	NPD6280	Approved
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5763	Approved
0.6646	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD2353	Approved
0.6646	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6832	Phase 2
0.6631	Remote Similarity	NPD2491	Approved
0.6626	Remote Similarity	NPD5049	Phase 3
0.6625	Remote Similarity	NPD7003	Approved
0.6625	Remote Similarity	NPD8166	Discontinued
0.6625	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD8032	Phase 2
0.6613	Remote Similarity	NPD4107	Approved
0.6609	Remote Similarity	NPD7799	Discontinued
0.6608	Remote Similarity	NPD8127	Discontinued
0.6607	Remote Similarity	NPD2296	Approved
0.6604	Remote Similarity	NPD4534	Discontinued
0.6601	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8651	Approved
0.6597	Remote Similarity	NPD7157	Approved
0.6591	Remote Similarity	NPD6797	Phase 2
0.659	Remote Similarity	NPD2403	Approved
0.6585	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3140	Approved
0.6581	Remote Similarity	NPD4060	Phase 1
0.6581	Remote Similarity	NPD3142	Approved
0.6577	Remote Similarity	NPD9717	Approved
0.657	Remote Similarity	NPD3787	Discontinued
0.657	Remote Similarity	NPD6232	Discontinued
0.6568	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7907	Approved
0.6558	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7251	Discontinued
0.6552	Remote Similarity	NPD7473	Discontinued
0.6549	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4111	Phase 1
0.6548	Remote Similarity	NPD4665	Approved
0.6545	Remote Similarity	NPD7239	Suspended
0.6543	Remote Similarity	NPD3448	Approved
0.6538	Remote Similarity	NPD5735	Approved
0.6534	Remote Similarity	NPD7074	Phase 3
0.6532	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1651	Approved
0.6528	Remote Similarity	NPD5676	Approved
0.6522	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4308	Phase 3
0.6517	Remote Similarity	NPD7808	Phase 3
0.6517	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6233	Phase 2
0.6516	Remote Similarity	NPD4062	Phase 3
0.6514	Remote Similarity	NPD7177	Discontinued
0.6513	Remote Similarity	NPD5647	Approved
0.6506	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2424	Discontinued
0.649	Remote Similarity	NPD1283	Approved
0.649	Remote Similarity	NPD6696	Suspended
0.6489	Remote Similarity	NPD4482	Phase 3
0.6484	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8313	Approved
0.648	Remote Similarity	NPD8312	Approved
0.6477	Remote Similarity	NPD7054	Approved
0.6474	Remote Similarity	NPD5711	Approved
0.6474	Remote Similarity	NPD4140	Approved
0.6474	Remote Similarity	NPD6808	Phase 2
0.6474	Remote Similarity	NPD5710	Approved
0.6464	Remote Similarity	NPD8150	Discontinued
0.6463	Remote Similarity	NPD4662	Approved
0.6463	Remote Similarity	NPD4661	Approved
0.6452	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3268	Approved
0.6452	Remote Similarity	NPD411	Approved
0.6447	Remote Similarity	NPD1470	Approved
0.6447	Remote Similarity	NPD1203	Approved
0.6444	Remote Similarity	NPD8407	Phase 2
0.6442	Remote Similarity	NPD3300	Phase 2
0.6441	Remote Similarity	NPD7472	Approved
0.6438	Remote Similarity	NPD6005	Phase 3
0.6438	Remote Similarity	NPD6002	Phase 3
0.6438	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6004	Phase 3
0.6438	Remote Similarity	NPD6003	Clinical (unspecified phase)

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