NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	438.24
Volume:	460.898
LogP:	4.836
LogD:	3.556
LogS:	-4.662
# Rotatable Bonds:	4
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	5.531
Fsp3:	0.667
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:	-5.577
MDCK Permeability:	2.144775316992309e-05
Pgp-inhibitor:	0.11
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.412
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	96.40906524658203%
Volume Distribution (VD):	0.387
Pgp-substrate:	4.641518592834473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.522
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.462
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.67
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	2.795
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.221
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.198
Skin Sensitization:	0.178
Carcinogencity:	0.354
Eye Corrosion:	0.013
Eye Irritation:	0.069
Respiratory Toxicity:	0.67

Download Data

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

Natural Product: NPC329913

Natural Product ID:	NPC329913
*Common Name:**	4-epi-Scopadulcic Acid B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DQBAMWXMUCSBLO-CADUKSBLSA-N
Standard InCHI:	InChI=1S/C27H34O5/c1-24-12-13-27(16-24)18(15-20(24)28)14-19(32-22(29)17-8-5-4-6-9-17)21-25(2,23(30)31)10-7-11-26(21,27)3/h4-6,8-9,18-19,21H,7,10-16H2,1-3H3,(H,30,31)/t18-,19+,21-,24+,25-,26-,27-/m0/s1
SMILES:	O=C(c1ccccc1)O[C@@H]1C[C@H]2CC(=O)[C@]3(C[C@@]2([C@@]2([C@@H]1[C@](C)(CCC2)C(=O)O)C)CC3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509623
PubChem CID:	10917156
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
ED50	6
IC50	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3045	Cell Line	NUGC-4	Homo sapiens	ED50	=	109.9	uM	PMID[549622]
NPT1618	Individual Protein	Peroxisome proliferator-activated receptor gamma	Mus musculus	EC50	>	100000.0	nM	PMID[549623]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	37.0	uM	PMID[549622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	136.9	uM	PMID[549622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	59.3	uM	PMID[549622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	48.3	uM	PMID[549622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	124.3	uM	PMID[549622]
NPT2	Others	Unspecified		IC50	=	14600.0	nM	PMID[549623]

☑ 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 NPC329913 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	280
0.1-0.2	1110
0.2-0.3	2086
0.3-0.4	4277
0.4-0.5	8975
0.5-0.6	13544
0.6-0.7	10442
0.7-0.8	1647
0.8-0.85	231
0.85-0.9	96
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC126516
0.9385	High Similarity	NPC48929
0.9385	High Similarity	NPC203486
0.916	High Similarity	NPC472656
0.9141	High Similarity	NPC473220
0.9141	High Similarity	NPC470753
0.9141	High Similarity	NPC169913
0.9062	High Similarity	NPC470765
0.9062	High Similarity	NPC275576
0.8881	High Similarity	NPC477896
0.8881	High Similarity	NPC477893
0.8864	High Similarity	NPC470278
0.8722	High Similarity	NPC72915
0.8662	High Similarity	NPC250046
0.8662	High Similarity	NPC81698
0.8662	High Similarity	NPC60509
0.8647	High Similarity	NPC147561
0.8636	High Similarity	NPC115797
0.8636	High Similarity	NPC51448
0.8633	High Similarity	NPC475135
0.8613	High Similarity	NPC475373
0.8601	High Similarity	NPC165260
0.8601	High Similarity	NPC161239
0.8601	High Similarity	NPC198455
0.8601	High Similarity	NPC7095
0.8601	High Similarity	NPC112216
0.8582	High Similarity	NPC127857
0.8571	High Similarity	NPC477468
0.8571	High Similarity	NPC477894
0.8571	High Similarity	NPC163087
0.8542	High Similarity	NPC279442
0.8521	High Similarity	NPC473602
0.8511	High Similarity	NPC472569
0.8511	High Similarity	NPC70716
0.8511	High Similarity	NPC125106
0.8511	High Similarity	NPC476974
0.8511	High Similarity	NPC163719
0.8511	High Similarity	NPC241951
0.8511	High Similarity	NPC470152
0.8511	High Similarity	NPC25768
0.8511	High Similarity	NPC57628
0.8511	High Similarity	NPC95265
0.8511	High Similarity	NPC188865
0.8511	High Similarity	NPC472570
0.8511	High Similarity	NPC475122
0.8511	High Similarity	NPC472573
0.8511	High Similarity	NPC11685
0.8511	High Similarity	NPC95810
0.8511	High Similarity	NPC475759
0.85	High Similarity	NPC182869
0.85	High Similarity	NPC183540
0.8493	Intermediate Similarity	NPC282239
0.8489	Intermediate Similarity	NPC90614
0.8489	Intermediate Similarity	NPC100913
0.8489	Intermediate Similarity	NPC275592
0.8489	Intermediate Similarity	NPC171207
0.8489	Intermediate Similarity	NPC97667
0.8483	Intermediate Similarity	NPC477905
0.8478	Intermediate Similarity	NPC283375
0.8478	Intermediate Similarity	NPC183122
0.8472	Intermediate Similarity	NPC125033
0.8451	Intermediate Similarity	NPC184817
0.8451	Intermediate Similarity	NPC470159
0.8451	Intermediate Similarity	NPC70403
0.8451	Intermediate Similarity	NPC96903
0.8451	Intermediate Similarity	NPC158663
0.8451	Intermediate Similarity	NPC177940
0.8451	Intermediate Similarity	NPC171525
0.8451	Intermediate Similarity	NPC476973
0.8451	Intermediate Similarity	NPC469349
0.8451	Intermediate Similarity	NPC472556
0.8451	Intermediate Similarity	NPC29704
0.8451	Intermediate Similarity	NPC473088
0.8451	Intermediate Similarity	NPC174982
0.8451	Intermediate Similarity	NPC472568
0.8451	Intermediate Similarity	NPC472571
0.8451	Intermediate Similarity	NPC200471
0.8451	Intermediate Similarity	NPC472572
0.8451	Intermediate Similarity	NPC472575
0.8451	Intermediate Similarity	NPC471104
0.8451	Intermediate Similarity	NPC470157
0.845	Intermediate Similarity	NPC473243
0.844	Intermediate Similarity	NPC91703
0.8435	Intermediate Similarity	NPC106895
0.8435	Intermediate Similarity	NPC217091
0.8429	Intermediate Similarity	NPC16912
0.8429	Intermediate Similarity	NPC27377
0.8429	Intermediate Similarity	NPC224491
0.8429	Intermediate Similarity	NPC41481
0.8429	Intermediate Similarity	NPC291599
0.8429	Intermediate Similarity	NPC97947
0.8429	Intermediate Similarity	NPC472576
0.8429	Intermediate Similarity	NPC87448
0.8429	Intermediate Similarity	NPC118080
0.8425	Intermediate Similarity	NPC304876
0.8425	Intermediate Similarity	NPC265395
0.8425	Intermediate Similarity	NPC158333
0.8425	Intermediate Similarity	NPC1173
0.8425	Intermediate Similarity	NPC472005
0.8425	Intermediate Similarity	NPC257213
0.8425	Intermediate Similarity	NPC249471
0.8425	Intermediate Similarity	NPC77719
0.8425	Intermediate Similarity	NPC256142
0.8425	Intermediate Similarity	NPC473414
0.8425	Intermediate Similarity	NPC242262
0.8425	Intermediate Similarity	NPC472030
0.8425	Intermediate Similarity	NPC472022
0.8425	Intermediate Similarity	NPC237549
0.8417	Intermediate Similarity	NPC210591
0.8417	Intermediate Similarity	NPC472371
0.8417	Intermediate Similarity	NPC475652
0.8417	Intermediate Similarity	NPC214550
0.8417	Intermediate Similarity	NPC472395
0.8414	Intermediate Similarity	NPC101043
0.8414	Intermediate Similarity	NPC306799
0.8414	Intermediate Similarity	NPC471103
0.8414	Intermediate Similarity	NPC51602
0.8406	Intermediate Similarity	NPC472374
0.8406	Intermediate Similarity	NPC472372
0.8406	Intermediate Similarity	NPC472551
0.8406	Intermediate Similarity	NPC472545
0.8403	Intermediate Similarity	NPC473215
0.8394	Intermediate Similarity	NPC474608
0.8392	Intermediate Similarity	NPC475552
0.8382	Intermediate Similarity	NPC472394
0.8378	Intermediate Similarity	NPC472393
0.837	Intermediate Similarity	NPC272946
0.837	Intermediate Similarity	NPC475138
0.8367	Intermediate Similarity	NPC114410
0.8367	Intermediate Similarity	NPC112523
0.8367	Intermediate Similarity	NPC228204
0.8367	Intermediate Similarity	NPC26033
0.8357	Intermediate Similarity	NPC200592
0.8357	Intermediate Similarity	NPC473112
0.8357	Intermediate Similarity	NPC473085
0.8357	Intermediate Similarity	NPC147880
0.8357	Intermediate Similarity	NPC184747
0.8357	Intermediate Similarity	NPC473109
0.8357	Intermediate Similarity	NPC43241
0.8357	Intermediate Similarity	NPC473758
0.8357	Intermediate Similarity	NPC248287
0.8357	Intermediate Similarity	NPC79921
0.8357	Intermediate Similarity	NPC473060
0.8357	Intermediate Similarity	NPC473613
0.8357	Intermediate Similarity	NPC211137
0.8357	Intermediate Similarity	NPC48017
0.8357	Intermediate Similarity	NPC472547
0.8357	Intermediate Similarity	NPC234548
0.8357	Intermediate Similarity	NPC473081
0.8357	Intermediate Similarity	NPC475400
0.8357	Intermediate Similarity	NPC4341
0.8357	Intermediate Similarity	NPC476094
0.8356	Intermediate Similarity	NPC472548
0.8345	Intermediate Similarity	NPC39549
0.8345	Intermediate Similarity	NPC254558
0.8345	Intermediate Similarity	NPC470245
0.8345	Intermediate Similarity	NPC473214
0.8333	Intermediate Similarity	NPC17877
0.8333	Intermediate Similarity	NPC291638
0.8333	Intermediate Similarity	NPC66761
0.8333	Intermediate Similarity	NPC140118
0.8333	Intermediate Similarity	NPC472577
0.8333	Intermediate Similarity	NPC12881
0.8333	Intermediate Similarity	NPC281717
0.8333	Intermediate Similarity	NPC195647
0.8322	Intermediate Similarity	NPC471107
0.8322	Intermediate Similarity	NPC471102
0.8322	Intermediate Similarity	NPC471100
0.831	Intermediate Similarity	NPC95449
0.8299	Intermediate Similarity	NPC472658
0.8299	Intermediate Similarity	NPC472657
0.8276	Intermediate Similarity	NPC473403
0.8276	Intermediate Similarity	NPC301556
0.8276	Intermediate Similarity	NPC476975
0.8276	Intermediate Similarity	NPC266265
0.8276	Intermediate Similarity	NPC270590
0.8276	Intermediate Similarity	NPC92293
0.8276	Intermediate Similarity	NPC471101
0.8271	Intermediate Similarity	NPC295664
0.8264	Intermediate Similarity	NPC474935
0.8261	Intermediate Similarity	NPC477368
0.8261	Intermediate Similarity	NPC477359
0.8261	Intermediate Similarity	NPC310662
0.8255	Intermediate Similarity	NPC469417
0.8255	Intermediate Similarity	NPC469771
0.8254	Intermediate Similarity	NPC128368
0.8252	Intermediate Similarity	NPC470231
0.8244	Intermediate Similarity	NPC50872
0.8243	Intermediate Similarity	NPC469456
0.8243	Intermediate Similarity	NPC21410
0.8243	Intermediate Similarity	NPC472549
0.8243	Intermediate Similarity	NPC473611
0.8243	Intermediate Similarity	NPC473670
0.8243	Intermediate Similarity	NPC132599
0.8243	Intermediate Similarity	NPC473632
0.8243	Intermediate Similarity	NPC469730
0.8235	Intermediate Similarity	NPC477491
0.8235	Intermediate Similarity	NPC471832
0.8231	Intermediate Similarity	NPC202015
0.8227	Intermediate Similarity	NPC473440

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 NPC329913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	749
0.2-0.3	1289
0.3-0.4	2585
0.4-0.5	2493
0.5-0.6	1325
0.6-0.7	443
0.7-0.8	33
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8986	High Similarity	NPD7236	Approved
0.8671	High Similarity	NPD7239	Suspended
0.8248	Intermediate Similarity	NPD7961	Discontinued
0.8146	Intermediate Similarity	NPD7057	Phase 3
0.8146	Intermediate Similarity	NPD7058	Phase 2
0.8102	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD7008	Discontinued
0.7905	Intermediate Similarity	NPD6273	Approved
0.7895	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7610	Discontinued
0.7799	Intermediate Similarity	NPD7799	Discontinued
0.7748	Intermediate Similarity	NPD7458	Discontinued
0.771	Intermediate Similarity	NPD5951	Approved
0.7704	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6858	Approved
0.7692	Intermediate Similarity	NPD7094	Approved
0.7687	Intermediate Similarity	NPD8166	Discontinued
0.7656	Intermediate Similarity	NPD2182	Approved
0.7603	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7003	Approved
0.7519	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD8127	Discontinued
0.7483	Intermediate Similarity	NPD6663	Approved
0.7466	Intermediate Similarity	NPD7305	Phase 1
0.7447	Intermediate Similarity	NPD5736	Approved
0.7444	Intermediate Similarity	NPD2629	Approved
0.7391	Intermediate Similarity	NPD6287	Discontinued
0.7388	Intermediate Similarity	NPD4198	Discontinued
0.7376	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2346	Discontinued
0.7348	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD164	Approved
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7292	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1930	Approved
0.7266	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1929	Approved
0.7255	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8032	Phase 2
0.723	Intermediate Similarity	NPD2799	Discontinued
0.7226	Intermediate Similarity	NPD7741	Discontinued
0.7215	Intermediate Similarity	NPD5761	Phase 2
0.7215	Intermediate Similarity	NPD5760	Phase 2
0.7186	Intermediate Similarity	NPD8368	Discontinued
0.7179	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2313	Discontinued
0.7165	Intermediate Similarity	NPD1238	Approved
0.7165	Intermediate Similarity	NPD2066	Phase 3
0.716	Intermediate Similarity	NPD8407	Phase 2
0.7133	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6085	Phase 2
0.7132	Intermediate Similarity	NPD6647	Phase 2
0.7123	Intermediate Similarity	NPD7713	Phase 3
0.7122	Intermediate Similarity	NPD3019	Approved
0.7107	Intermediate Similarity	NPD7819	Suspended
0.7101	Intermediate Similarity	NPD7009	Phase 2
0.7093	Intermediate Similarity	NPD8435	Approved
0.7093	Intermediate Similarity	NPD8361	Approved
0.7093	Intermediate Similarity	NPD8360	Approved
0.7092	Intermediate Similarity	NPD3972	Approved
0.7083	Intermediate Similarity	NPD6764	Approved
0.7083	Intermediate Similarity	NPD6765	Approved
0.7076	Intermediate Similarity	NPD8434	Phase 2
0.7075	Intermediate Similarity	NPD4140	Approved
0.707	Intermediate Similarity	NPD3226	Approved
0.703	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7018	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2932	Approved
0.6993	Remote Similarity	NPD1876	Approved
0.6985	Remote Similarity	NPD6010	Discontinued
0.6978	Remote Similarity	NPD9545	Approved
0.6972	Remote Similarity	NPD4878	Approved
0.6962	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2935	Discontinued
0.6954	Remote Similarity	NPD5405	Approved
0.6954	Remote Similarity	NPD5408	Approved
0.6954	Remote Similarity	NPD5404	Approved
0.6954	Remote Similarity	NPD5406	Approved
0.695	Remote Similarity	NPD3023	Approved
0.695	Remote Similarity	NPD3026	Approved
0.6949	Remote Similarity	NPD8485	Approved
0.6947	Remote Similarity	NPD1237	Approved
0.6947	Remote Similarity	NPD5909	Discontinued
0.694	Remote Similarity	NPD2067	Discontinued
0.6934	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7097	Phase 1
0.6929	Remote Similarity	NPD3025	Approved
0.6929	Remote Similarity	NPD3024	Approved
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD1932	Approved
0.6923	Remote Similarity	NPD2532	Approved
0.6919	Remote Similarity	NPD6784	Approved
0.6919	Remote Similarity	NPD6785	Approved
0.6905	Remote Similarity	NPD5844	Phase 1
0.6897	Remote Similarity	NPD2798	Approved
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7714	Approved
0.6892	Remote Similarity	NPD7715	Approved
0.6886	Remote Similarity	NPD7473	Discontinued
0.6883	Remote Similarity	NPD4110	Phase 3
0.6883	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD1283	Approved
0.6875	Remote Similarity	NPD7411	Suspended
0.6866	Remote Similarity	NPD2329	Discontinued
0.6852	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1693	Approved
0.6846	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2979	Phase 3
0.6833	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1470	Approved
0.6824	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6599	Discontinued
0.6813	Remote Similarity	NPD7497	Discontinued
0.6813	Remote Similarity	NPD7028	Phase 2
0.681	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7768	Phase 2
0.6809	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7055	Discontinued
0.6802	Remote Similarity	NPD8312	Approved
0.6802	Remote Similarity	NPD8313	Approved
0.68	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1471	Phase 3
0.6774	Remote Similarity	NPD3750	Approved
0.6774	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7075	Discontinued
0.6763	Remote Similarity	NPD3317	Approved
0.6755	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6959	Discontinued
0.6746	Remote Similarity	NPD7177	Discontinued
0.6736	Remote Similarity	NPD1608	Approved
0.6727	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6685	Approved
0.6712	Remote Similarity	NPD2797	Approved
0.6711	Remote Similarity	NPD6798	Discontinued
0.6709	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4380	Phase 2
0.6707	Remote Similarity	NPD6232	Discontinued
0.6693	Remote Similarity	NPD1088	Approved
0.669	Remote Similarity	NPD5327	Phase 3
0.6689	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD2344	Approved
0.6688	Remote Similarity	NPD5763	Approved
0.6688	Remote Similarity	NPD5762	Approved
0.6687	Remote Similarity	NPD5494	Approved
0.6686	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1201	Approved
0.6646	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7390	Discontinued
0.6645	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6353	Approved
0.6644	Remote Similarity	NPD7095	Approved
0.6644	Remote Similarity	NPD6039	Approved
0.6643	Remote Similarity	NPD5126	Approved
0.6643	Remote Similarity	NPD5125	Phase 3
0.6643	Remote Similarity	NPD3095	Discontinued
0.6643	Remote Similarity	NPD7115	Discovery
0.6641	Remote Similarity	NPD1202	Approved
0.6626	Remote Similarity	NPD37	Approved
0.6624	Remote Similarity	NPD6190	Approved
0.6623	Remote Similarity	NPD6099	Approved
0.6623	Remote Similarity	NPD6100	Approved
0.6623	Remote Similarity	NPD2438	Suspended
0.6623	Remote Similarity	NPD2796	Approved
0.662	Remote Similarity	NPD3091	Approved
0.6619	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3495	Discontinued
0.6615	Remote Similarity	NPD7902	Approved
0.6607	Remote Similarity	NPD7229	Phase 3
0.6606	Remote Similarity	NPD4966	Approved
0.6606	Remote Similarity	NPD4965	Approved
0.6606	Remote Similarity	NPD4967	Phase 2
0.6604	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3267	Approved
0.6599	Remote Similarity	NPD3266	Approved
0.6597	Remote Similarity	NPD4879	Approved
0.6596	Remote Similarity	NPD9493	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