NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	498.26
Volume:	524.911
LogP:	3.851
LogD:	3.441
LogS:	-4.107
# Rotatable Bonds:	10
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	4.507
Fsp3:	0.552
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:	-5.58
MDCK Permeability:	8.01360874902457e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.658
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.362

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.866
Plasma Protein Binding (PPB):	73.62149047851562%
Volume Distribution (VD):	0.285
Pgp-substrate:	26.41814422607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	2.28
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.83
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.525
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.44
Carcinogencity:	0.213
Eye Corrosion:	0.01
Eye Irritation:	0.123
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC477893

Natural Product ID:	NPC477893
*Common Name:**	(1S,4aR,5S,7S,8S,8aR)-7-acetyloxy-8-benzoyloxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
IUPAC Name:	(1S,4aR,5S,7S,8S,8aR)-7-acetyloxy-8-benzoyloxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	GIZWHSIXXJICSK-NFSQIVDPSA-N
Standard InCHI:	InChI=1S/C29H38O7/c1-18(14-17-30)12-13-22-19(2)23(35-20(3)31)24(36-26(32)21-10-7-6-8-11-21)25-28(22,4)15-9-16-29(25,5)27(33)34/h6-8,10-11,14,22-25,30H,2,9,12-13,15-17H2,1,3-5H3,(H,33,34)/b18-14+/t22-,23+,24-,25-,28-,29+/m1/s1
SMILES:	C/C(=C\CO)/CC[C@@H]1C(=C)[C@@H]([C@H]([C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C)OC(=O)C3=CC=CC=C3)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118707630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1618	Individual Protein	Peroxisome proliferator-activated receptor gamma	Mus musculus	EC50	=	900	nM	PMID[24955889]

☑ 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 NPC477893 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	279
0.1-0.2	1034
0.2-0.3	2114
0.3-0.4	4199
0.4-0.5	8349
0.5-0.6	11258
0.6-0.7	12004
0.7-0.8	3027
0.8-0.85	222
0.85-0.9	204
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC477896
0.9478	High Similarity	NPC477894
0.937	High Similarity	NPC169913
0.9291	High Similarity	NPC275576
0.9259	High Similarity	NPC182869
0.9173	High Similarity	NPC472374
0.9173	High Similarity	NPC472372
0.9111	High Similarity	NPC90614
0.9111	High Similarity	NPC100913
0.9111	High Similarity	NPC275592
0.9058	High Similarity	NPC127857
0.9044	High Similarity	NPC27377
0.9044	High Similarity	NPC41481
0.9044	High Similarity	NPC97947
0.9044	High Similarity	NPC472576
0.9044	High Similarity	NPC118080
0.9044	High Similarity	NPC87448
0.9044	High Similarity	NPC291599
0.9023	High Similarity	NPC48929
0.9	High Similarity	NPC60509
0.9	High Similarity	NPC250046
0.9	High Similarity	NPC81698
0.8971	High Similarity	NPC472547
0.8971	High Similarity	NPC97667
0.8971	High Similarity	NPC171207
0.8963	High Similarity	NPC39549
0.8936	High Similarity	NPC161239
0.8936	High Similarity	NPC7095
0.8936	High Similarity	NPC198455
0.8936	High Similarity	NPC165260
0.8921	High Similarity	NPC472556
0.8913	High Similarity	NPC91703
0.8913	High Similarity	NPC163087
0.8913	High Similarity	NPC95449
0.8905	High Similarity	NPC16912
0.8889	High Similarity	NPC472551
0.8889	High Similarity	NPC472545
0.8881	High Similarity	NPC474608
0.8881	High Similarity	NPC329913
0.8881	High Similarity	NPC126516
0.8873	High Similarity	NPC471103
0.8873	High Similarity	NPC197037
0.8849	High Similarity	NPC241951
0.8849	High Similarity	NPC470152
0.8849	High Similarity	NPC475759
0.8849	High Similarity	NPC38696
0.8849	High Similarity	NPC475122
0.8841	High Similarity	NPC34012
0.8819	High Similarity	NPC21410
0.8819	High Similarity	NPC469730
0.8819	High Similarity	NPC132599
0.8819	High Similarity	NPC473632
0.8819	High Similarity	NPC473670
0.8815	High Similarity	NPC472577
0.8815	High Similarity	NPC195647
0.8815	High Similarity	NPC66761
0.8815	High Similarity	NPC17877
0.8815	High Similarity	NPC291638
0.8811	High Similarity	NPC472548
0.8811	High Similarity	NPC477905
0.8803	High Similarity	NPC91730
0.8803	High Similarity	NPC112216
0.8786	High Similarity	NPC472572
0.8786	High Similarity	NPC200471
0.8786	High Similarity	NPC472568
0.8786	High Similarity	NPC96903
0.8786	High Similarity	NPC174982
0.8786	High Similarity	NPC470157
0.8786	High Similarity	NPC472571
0.8786	High Similarity	NPC476973
0.8786	High Similarity	NPC472575
0.8786	High Similarity	NPC469349
0.8786	High Similarity	NPC70403
0.8786	High Similarity	NPC473088
0.8786	High Similarity	NPC471104
0.8786	High Similarity	NPC470159
0.8786	High Similarity	NPC158663
0.8786	High Similarity	NPC171525
0.8786	High Similarity	NPC184817
0.8786	High Similarity	NPC177940
0.8786	High Similarity	NPC29704
0.8768	High Similarity	NPC224491
0.8759	High Similarity	NPC9905
0.875	High Similarity	NPC472022
0.875	High Similarity	NPC472005
0.875	High Similarity	NPC134685
0.875	High Similarity	NPC256142
0.875	High Similarity	NPC304876
0.875	High Similarity	NPC237549
0.875	High Similarity	NPC248265
0.875	High Similarity	NPC265395
0.875	High Similarity	NPC257213
0.875	High Similarity	NPC473414
0.875	High Similarity	NPC472030
0.875	High Similarity	NPC1173
0.875	High Similarity	NPC242262
0.875	High Similarity	NPC158333
0.875	High Similarity	NPC11588
0.875	High Similarity	NPC229545
0.875	High Similarity	NPC249471
0.8741	High Similarity	NPC306799
0.8741	High Similarity	NPC51602
0.8741	High Similarity	NPC101043
0.8731	High Similarity	NPC472394
0.8722	High Similarity	NPC147561
0.8714	High Similarity	NPC57628
0.8714	High Similarity	NPC11685
0.8714	High Similarity	NPC95265
0.8714	High Similarity	NPC70716
0.8714	High Similarity	NPC472569
0.8714	High Similarity	NPC125106
0.8714	High Similarity	NPC163719
0.8714	High Similarity	NPC472573
0.8714	High Similarity	NPC95810
0.8714	High Similarity	NPC188865
0.8714	High Similarity	NPC34943
0.8714	High Similarity	NPC476974
0.8714	High Similarity	NPC472570
0.8714	High Similarity	NPC25768
0.8705	High Similarity	NPC192658
0.8696	High Similarity	NPC162613
0.8696	High Similarity	NPC87934
0.869	High Similarity	NPC155329
0.869	High Similarity	NPC473611
0.869	High Similarity	NPC112523
0.869	High Similarity	NPC228204
0.869	High Similarity	NPC26033
0.869	High Similarity	NPC114410
0.869	High Similarity	NPC259144
0.869	High Similarity	NPC472549
0.869	High Similarity	NPC114357
0.8686	High Similarity	NPC283375
0.8686	High Similarity	NPC183122
0.8662	High Similarity	NPC132652
0.8662	High Similarity	NPC217918
0.8662	High Similarity	NPC473760
0.8657	High Similarity	NPC72915
0.8652	High Similarity	NPC92867
0.8652	High Similarity	NPC125882
0.8652	High Similarity	NPC471100
0.8652	High Similarity	NPC311825
0.8652	High Similarity	NPC471107
0.8643	High Similarity	NPC477468
0.8636	High Similarity	NPC473220
0.8636	High Similarity	NPC470753
0.8636	High Similarity	NPC253681
0.8633	High Similarity	NPC266374
0.863	High Similarity	NPC106895
0.8623	High Similarity	NPC210591
0.8623	High Similarity	NPC214550
0.8623	High Similarity	NPC475652
0.8621	High Similarity	NPC77719
0.8621	High Similarity	NPC219419
0.8611	High Similarity	NPC470153
0.8603	High Similarity	NPC203486
0.8601	High Similarity	NPC301556
0.8601	High Similarity	NPC270590
0.8601	High Similarity	NPC92293
0.8601	High Similarity	NPC473215
0.8601	High Similarity	NPC476975
0.8601	High Similarity	NPC471101
0.8601	High Similarity	NPC266265
0.8592	High Similarity	NPC209592
0.8592	High Similarity	NPC473602
0.8592	High Similarity	NPC240115
0.8592	High Similarity	NPC20255
0.8592	High Similarity	NPC48599
0.8592	High Similarity	NPC474935
0.8582	High Similarity	NPC472388
0.8571	High Similarity	NPC469417
0.8571	High Similarity	NPC472546
0.8571	High Similarity	NPC475135
0.8571	High Similarity	NPC469771
0.8562	High Similarity	NPC282239
0.8561	High Similarity	NPC184747
0.8561	High Similarity	NPC470765
0.8561	High Similarity	NPC473060
0.8561	High Similarity	NPC43241
0.8561	High Similarity	NPC473081
0.8561	High Similarity	NPC473758
0.8561	High Similarity	NPC211137
0.8561	High Similarity	NPC473613
0.8561	High Similarity	NPC477904
0.8561	High Similarity	NPC200592
0.8561	High Similarity	NPC48017
0.8561	High Similarity	NPC183270
0.8561	High Similarity	NPC147880
0.8561	High Similarity	NPC476094
0.8561	High Similarity	NPC473109
0.8561	High Similarity	NPC473112
0.8561	High Similarity	NPC4341
0.8561	High Similarity	NPC473085
0.8552	High Similarity	NPC469647
0.8552	High Similarity	NPC22571
0.8552	High Similarity	NPC327962
0.8552	High Similarity	NPC469648
0.8552	High Similarity	NPC138641
0.8552	High Similarity	NPC283875
0.8542	High Similarity	NPC473214
0.8542	High Similarity	NPC470245

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 NPC477893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	730
0.2-0.3	1384
0.3-0.4	2524
0.4-0.5	2308
0.5-0.6	1411
0.6-0.7	493
0.7-0.8	62
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
0.8264	Intermediate Similarity	NPD7236	Approved
0.8175	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7987	Intermediate Similarity	NPD7239	Suspended
0.7923	Intermediate Similarity	NPD2629	Approved
0.7786	Intermediate Similarity	NPD7008	Discontinued
0.775	Intermediate Similarity	NPD7799	Discontinued
0.7698	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD8368	Discontinued
0.7652	Intermediate Similarity	NPD5951	Approved
0.7615	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3764	Approved
0.7597	Intermediate Similarity	NPD2182	Approved
0.7597	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7458	Discontinued
0.7568	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8360	Approved
0.756	Intermediate Similarity	NPD8361	Approved
0.7545	Intermediate Similarity	NPD8434	Phase 2
0.7545	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8407	Phase 2
0.7517	Intermediate Similarity	NPD8166	Discontinued
0.7516	Intermediate Similarity	NPD7057	Phase 3
0.7516	Intermediate Similarity	NPD7058	Phase 2
0.7485	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7467	Intermediate Similarity	NPD6190	Approved
0.7463	Intermediate Similarity	NPD4198	Discontinued
0.7456	Intermediate Similarity	NPD8435	Approved
0.7445	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD8127	Discontinued
0.7426	Intermediate Similarity	NPD7741	Discontinued
0.7426	Intermediate Similarity	NPD9545	Approved
0.7405	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6273	Approved
0.7379	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7473	Discontinued
0.7337	Intermediate Similarity	NPD8150	Discontinued
0.7329	Intermediate Similarity	NPD230	Phase 1
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7961	Discontinued
0.7299	Intermediate Similarity	NPD8485	Approved
0.7287	Intermediate Similarity	NPD164	Approved
0.7285	Intermediate Similarity	NPD7003	Approved
0.7284	Intermediate Similarity	NPD6232	Discontinued
0.7278	Intermediate Similarity	NPD5761	Phase 2
0.7278	Intermediate Similarity	NPD5760	Phase 2
0.7278	Intermediate Similarity	NPD7819	Suspended
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7075	Discontinued
0.7244	Intermediate Similarity	NPD3226	Approved
0.7244	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.7192	Intermediate Similarity	NPD6663	Approved
0.7188	Intermediate Similarity	NPD4966	Approved
0.7188	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4965	Approved
0.7181	Intermediate Similarity	NPD7305	Phase 1
0.7176	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5736	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1238	Approved
0.7107	Intermediate Similarity	NPD6801	Discontinued
0.7099	Intermediate Similarity	NPD5048	Discontinued
0.7097	Intermediate Similarity	NPD2533	Approved
0.7097	Intermediate Similarity	NPD2532	Approved
0.7097	Intermediate Similarity	NPD2534	Approved
0.7092	Intermediate Similarity	NPD6287	Discontinued
0.7089	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD2346	Discontinued
0.7077	Intermediate Similarity	NPD1929	Approved
0.7077	Intermediate Similarity	NPD1930	Approved
0.7077	Intermediate Similarity	NPD6647	Phase 2
0.7077	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5125	Phase 3
0.7071	Intermediate Similarity	NPD5126	Approved
0.7069	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2799	Discontinued
0.7063	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD8312	Approved
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7411	Suspended
0.7042	Intermediate Similarity	NPD1608	Approved
0.7041	Intermediate Similarity	NPD7685	Pre-registration
0.7041	Intermediate Similarity	NPD6764	Approved
0.7041	Intermediate Similarity	NPD6765	Approved
0.7039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1237	Approved
0.7023	Intermediate Similarity	NPD5909	Discontinued
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2067	Discontinued
0.7007	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD1934	Approved
0.6994	Remote Similarity	NPD6234	Discontinued
0.6985	Remote Similarity	NPD6858	Approved
0.6985	Remote Similarity	NPD7094	Approved
0.6982	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6355	Discontinued
0.6975	Remote Similarity	NPD7768	Phase 2
0.6974	Remote Similarity	NPD7266	Discontinued
0.6974	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6085	Phase 2
0.6963	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5494	Approved
0.6948	Remote Similarity	NPD3750	Approved
0.6937	Remote Similarity	NPD6386	Approved
0.6937	Remote Similarity	NPD6385	Approved
0.6934	Remote Similarity	NPD6010	Discontinued
0.6933	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6799	Approved
0.6914	Remote Similarity	NPD3817	Phase 2
0.6914	Remote Similarity	NPD5402	Approved
0.6908	Remote Similarity	NPD5404	Approved
0.6908	Remote Similarity	NPD5405	Approved
0.6908	Remote Similarity	NPD5406	Approved
0.6908	Remote Similarity	NPD5408	Approved
0.6905	Remote Similarity	NPD7228	Approved
0.6905	Remote Similarity	NPD3818	Discontinued
0.6903	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1470	Approved
0.6892	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6798	Discontinued
0.6887	Remote Similarity	NPD7097	Phase 1
0.6886	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6166	Phase 2
0.6886	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6784	Approved
0.6879	Remote Similarity	NPD6785	Approved
0.6879	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6005	Phase 3
0.6863	Remote Similarity	NPD6004	Phase 3
0.6863	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6002	Phase 3
0.6857	Remote Similarity	NPD7610	Discontinued
0.6853	Remote Similarity	NPD4806	Approved
0.6853	Remote Similarity	NPD4807	Approved
0.6852	Remote Similarity	NPD8455	Phase 2
0.6852	Remote Similarity	NPD1465	Phase 2
0.6852	Remote Similarity	NPD2801	Approved
0.6846	Remote Similarity	NPD7714	Approved
0.6846	Remote Similarity	NPD2066	Phase 3
0.6846	Remote Similarity	NPD7715	Approved
0.6842	Remote Similarity	NPD1510	Phase 2
0.6842	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4110	Phase 3
0.6831	Remote Similarity	NPD5306	Approved
0.6831	Remote Similarity	NPD17	Approved
0.6831	Remote Similarity	NPD5305	Approved
0.6824	Remote Similarity	NPD7074	Phase 3
0.6824	Remote Similarity	NPD7095	Approved
0.6821	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1549	Phase 2
0.6807	Remote Similarity	NPD7199	Phase 2
0.6806	Remote Similarity	NPD3972	Approved
0.6805	Remote Similarity	NPD7177	Discontinued
0.68	Remote Similarity	NPD4140	Approved
0.6797	Remote Similarity	NPD6100	Approved
0.6797	Remote Similarity	NPD6099	Approved
0.6797	Remote Similarity	NPD2796	Approved
0.6792	Remote Similarity	NPD5403	Approved
0.6791	Remote Similarity	NPD6685	Approved
0.6788	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2797	Approved
0.6779	Remote Similarity	NPD3268	Approved
0.6776	Remote Similarity	NPD7497	Discontinued
0.6772	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9495	Approved
0.6768	Remote Similarity	NPD3882	Suspended
0.6766	Remote Similarity	NPD7229	Phase 3
0.6765	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7054	Approved
0.6761	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD447	Suspended
0.6753	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5763	Approved
0.6753	Remote Similarity	NPD5762	Approved
0.6739	Remote Similarity	NPD8320	Phase 1
0.6739	Remote Similarity	NPD8319	Approved
0.6736	Remote Similarity	NPD1201	Approved
0.6735	Remote Similarity	NPD2798	Approved
0.6733	Remote Similarity	NPD7713	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