NPASS Compound

Structure

CID48929 OpenBabel06191715382D 31 35 0 0 1 0 0 0 0 0999 V2000 -0.7853 -2.2484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0106 2.5757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7853 -0.4264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0480 1.8136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2860 1.3737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0480 2.6935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3560 0.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5240 1.8136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2860 3.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3560 1.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5707 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1215 -1.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4535 -0.7853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7854 1.3602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5707 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1307 2.5757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5240 2.6935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7853 0.4534 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.8137 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5707 -0.9069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7853 1.3603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7621 3.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7853 -1.3603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5706 1.8137 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7853 0.4534 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 1.5706 3.3377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3398 -1.3510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7621 4.0133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.6935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 16 27 1 0 0 0 0 17 25 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 19 27 1 6 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 24 1 1 0 0 0 21 29 1 0 0 0 0 22 25 1 1 0 0 0 22 26 1 0 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 24 1 1 6 0 0 0 25 2 1 1 0 0 0 26 27 1 6 0 0 0 27 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	457.381
LogP:	4.925
LogD:	4.091
LogS:	-4.513
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	5.665
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.952
MDCK Permeability:	2.52045392699074e-05
Pgp-inhibitor:	0.123
Pgp-substrate:	0.182
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.31
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	99.25646209716797%
Volume Distribution (VD):	0.888
Pgp-substrate:	2.791543483734131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.208
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.348

ADMET: Excretion

Clearance (CL):	10.235
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.796
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.749
Skin Sensitization:	0.942
Carcinogencity:	0.158
Eye Corrosion:	0.005
Eye Irritation:	0.117
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC48929

Natural Product ID:	NPC48929
*Common Name:**	Dulcidiol
IUPAC Name:	n.a.
Synonyms:	Dulcidiol
Standard InCHIKey:	GRHQTTJLYWYUIY-MMIHEUQKSA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-24-12-13-27(16-24)19(15-21(24)29)14-20(31-23(30)18-8-5-4-6-9-18)22-25(2,17-28)10-7-11-26(22,27)3/h4-6,8-9,19-22,28-29H,7,10-17H2,1-3H3/t19-,20+,21-,22-,24+,25-,26-,27-/m0/s1
SMILES:	C[C@@]12CC[C@]3(C1)[C@@H](C[C@H]([C@H]1[C@@](C)(CCC[C@]31C)CO)OC(=O)c1ccccc1)C[C@@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453808
PubChem CID:	11826069
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
ED50	6

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3045	Cell Line	NUGC-4	Homo sapiens	ED50	=	105.1	uM	PMID[493307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	45.3	uM	PMID[493307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	46.0	uM	PMID[493307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	42.6	uM	PMID[493307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	41.6	uM	PMID[493307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	29.0	uM	PMID[493307]

☑ 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 NPC48929 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	274
0.1-0.2	1030
0.2-0.3	2075
0.3-0.4	4049
0.4-0.5	8276
0.5-0.6	13639
0.6-0.7	11289
0.7-0.8	1631
0.8-0.85	237
0.85-0.9	130
0.9-0.95	64
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC126516
0.9385	High Similarity	NPC329913
0.9302	High Similarity	NPC72915
0.9237	High Similarity	NPC203486
0.9213	High Similarity	NPC275576
0.9141	High Similarity	NPC473220
0.9141	High Similarity	NPC169913
0.9141	High Similarity	NPC470753
0.9118	High Similarity	NPC163087
0.9077	High Similarity	NPC147561
0.9062	High Similarity	NPC470765
0.9058	High Similarity	NPC473602
0.9051	High Similarity	NPC241951
0.9051	High Similarity	NPC475122
0.9051	High Similarity	NPC470152
0.9051	High Similarity	NPC475759
0.9037	High Similarity	NPC90614
0.9037	High Similarity	NPC100913
0.9037	High Similarity	NPC275592
0.9023	High Similarity	NPC477893
0.8986	High Similarity	NPC472568
0.8986	High Similarity	NPC472575
0.8986	High Similarity	NPC471104
0.8986	High Similarity	NPC184817
0.8986	High Similarity	NPC96903
0.8986	High Similarity	NPC174982
0.8986	High Similarity	NPC158663
0.8986	High Similarity	NPC473088
0.8986	High Similarity	NPC476973
0.8986	High Similarity	NPC472571
0.8986	High Similarity	NPC469349
0.8986	High Similarity	NPC70403
0.8986	High Similarity	NPC470157
0.8986	High Similarity	NPC171525
0.8986	High Similarity	NPC29704
0.8986	High Similarity	NPC472556
0.8986	High Similarity	NPC177940
0.8986	High Similarity	NPC200471
0.8986	High Similarity	NPC472572
0.8986	High Similarity	NPC470159
0.8978	High Similarity	NPC91703
0.8971	High Similarity	NPC472576
0.8971	High Similarity	NPC27377
0.8971	High Similarity	NPC87448
0.8971	High Similarity	NPC291599
0.8971	High Similarity	NPC41481
0.8971	High Similarity	NPC97947
0.8971	High Similarity	NPC118080
0.8955	High Similarity	NPC472374
0.8955	High Similarity	NPC472372
0.8913	High Similarity	NPC472570
0.8913	High Similarity	NPC476974
0.8913	High Similarity	NPC95810
0.8913	High Similarity	NPC125106
0.8913	High Similarity	NPC95265
0.8913	High Similarity	NPC472573
0.8913	High Similarity	NPC11685
0.8913	High Similarity	NPC163719
0.8913	High Similarity	NPC70716
0.8913	High Similarity	NPC472569
0.8913	High Similarity	NPC25768
0.8913	High Similarity	NPC57628
0.8913	High Similarity	NPC188865
0.8897	High Similarity	NPC97667
0.8897	High Similarity	NPC472547
0.8897	High Similarity	NPC171207
0.8889	High Similarity	NPC283375
0.8889	High Similarity	NPC183122
0.8889	High Similarity	NPC39549
0.8889	High Similarity	NPC475373
0.8881	High Similarity	NPC477896
0.8832	High Similarity	NPC224491
0.8832	High Similarity	NPC16912
0.8824	High Similarity	NPC475652
0.8824	High Similarity	NPC214550
0.8824	High Similarity	NPC210591
0.8815	High Similarity	NPC472551
0.8815	High Similarity	NPC472545
0.8811	High Similarity	NPC472657
0.8811	High Similarity	NPC472658
0.8806	High Similarity	NPC474608
0.8803	High Similarity	NPC279442
0.8794	High Similarity	NPC476975
0.8794	High Similarity	NPC471101
0.8794	High Similarity	NPC266265
0.8794	High Similarity	NPC92293
0.8794	High Similarity	NPC473215
0.8794	High Similarity	NPC301556
0.8794	High Similarity	NPC270590
0.8759	High Similarity	NPC48017
0.8759	High Similarity	NPC4341
0.8759	High Similarity	NPC476094
0.8759	High Similarity	NPC473081
0.8759	High Similarity	NPC211137
0.8759	High Similarity	NPC184747
0.8759	High Similarity	NPC473613
0.8759	High Similarity	NPC473060
0.8759	High Similarity	NPC43241
0.8759	High Similarity	NPC473758
0.8759	High Similarity	NPC147880
0.8759	High Similarity	NPC473109
0.8759	High Similarity	NPC473085
0.8759	High Similarity	NPC200592
0.8759	High Similarity	NPC473112
0.8741	High Similarity	NPC472577
0.8741	High Similarity	NPC66761
0.8741	High Similarity	NPC291638
0.8741	High Similarity	NPC17877
0.8741	High Similarity	NPC195647
0.8732	High Similarity	NPC473214
0.8732	High Similarity	NPC470245
0.8731	High Similarity	NPC472656
0.8723	High Similarity	NPC281717
0.8722	High Similarity	NPC470278
0.8705	High Similarity	NPC477894
0.8671	High Similarity	NPC470153
0.8662	High Similarity	NPC81698
0.8662	High Similarity	NPC250046
0.8662	High Similarity	NPC60509
0.8652	High Similarity	NPC478263
0.8652	High Similarity	NPC474935
0.8633	High Similarity	NPC34012
0.8613	High Similarity	NPC262324
0.8611	High Similarity	NPC477905
0.8603	High Similarity	NPC473216
0.8603	High Similarity	NPC473399
0.8603	High Similarity	NPC471864
0.8601	High Similarity	NPC165260
0.8601	High Similarity	NPC161239
0.8601	High Similarity	NPC198455
0.8601	High Similarity	NPC7095
0.8601	High Similarity	NPC469448
0.8582	High Similarity	NPC478264
0.8571	High Similarity	NPC475429
0.8571	High Similarity	NPC477468
0.8571	High Similarity	NPC270498
0.8571	High Similarity	NPC147217
0.8571	High Similarity	NPC246480
0.8571	High Similarity	NPC473673
0.8571	High Similarity	NPC177340
0.8571	High Similarity	NPC191082
0.8571	High Similarity	NPC139067
0.8561	High Similarity	NPC266374
0.8551	High Similarity	NPC472395
0.8551	High Similarity	NPC9905
0.8551	High Similarity	NPC472371
0.8519	High Similarity	NPC238370
0.8519	High Similarity	NPC472394
0.8511	High Similarity	NPC38696
0.8511	High Similarity	NPC51314
0.8511	High Similarity	NPC67777
0.8511	High Similarity	NPC470231
0.8507	High Similarity	NPC475138
0.85	High Similarity	NPC192658
0.85	High Similarity	NPC475135
0.85	High Similarity	NPC182869
0.85	High Similarity	NPC183540
0.85	High Similarity	NPC472546
0.8489	Intermediate Similarity	NPC477904
0.8489	Intermediate Similarity	NPC87934
0.8489	Intermediate Similarity	NPC183270
0.8489	Intermediate Similarity	NPC79921
0.8489	Intermediate Similarity	NPC162613
0.8489	Intermediate Similarity	NPC475400
0.8483	Intermediate Similarity	NPC472548
0.8478	Intermediate Similarity	NPC243893
0.8473	Intermediate Similarity	NPC307139
0.8472	Intermediate Similarity	NPC477483
0.8472	Intermediate Similarity	NPC475417
0.8472	Intermediate Similarity	NPC325032
0.8472	Intermediate Similarity	NPC31829
0.8472	Intermediate Similarity	NPC112216
0.8472	Intermediate Similarity	NPC476173
0.8472	Intermediate Similarity	NPC475561
0.8462	Intermediate Similarity	NPC132652
0.8462	Intermediate Similarity	NPC473760
0.8451	Intermediate Similarity	NPC127857
0.8446	Intermediate Similarity	NPC476784
0.8435	Intermediate Similarity	NPC106895
0.8425	Intermediate Similarity	NPC304876
0.8425	Intermediate Similarity	NPC158333
0.8425	Intermediate Similarity	NPC1173
0.8425	Intermediate Similarity	NPC265395
0.8425	Intermediate Similarity	NPC257213
0.8425	Intermediate Similarity	NPC249471
0.8425	Intermediate Similarity	NPC472005
0.8425	Intermediate Similarity	NPC473414
0.8425	Intermediate Similarity	NPC242262
0.8425	Intermediate Similarity	NPC472030
0.8425	Intermediate Similarity	NPC256142
0.8425	Intermediate Similarity	NPC472022
0.8425	Intermediate Similarity	NPC237549
0.8421	Intermediate Similarity	NPC5486
0.8421	Intermediate Similarity	NPC253681
0.8414	Intermediate Similarity	NPC471103
0.8403	Intermediate Similarity	NPC76103
0.8392	Intermediate Similarity	NPC475552
0.8392	Intermediate Similarity	NPC312393
0.8392	Intermediate Similarity	NPC48599
0.8392	Intermediate Similarity	NPC209592

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 NPC48929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	709
0.2-0.3	1314
0.3-0.4	2572
0.4-0.5	2476
0.5-0.6	1371
0.6-0.7	443
0.7-0.8	36
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8714	High Similarity	NPD7236	Approved
0.8414	Intermediate Similarity	NPD7239	Suspended
0.8102	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD7008	Discontinued
0.8027	Intermediate Similarity	NPD6273	Approved
0.7986	Intermediate Similarity	NPD7961	Discontinued
0.7911	Intermediate Similarity	NPD7799	Discontinued
0.7908	Intermediate Similarity	NPD7057	Phase 3
0.7908	Intermediate Similarity	NPD7058	Phase 2
0.7883	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8127	Discontinued
0.7744	Intermediate Similarity	NPD7741	Discontinued
0.771	Intermediate Similarity	NPD5951	Approved
0.7674	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7610	Discontinued
0.7576	Intermediate Similarity	NPD2629	Approved
0.7574	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8166	Discontinued
0.7568	Intermediate Similarity	NPD7003	Approved
0.7568	Intermediate Similarity	NPD4628	Phase 3
0.7557	Intermediate Similarity	NPD6858	Approved
0.7557	Intermediate Similarity	NPD7094	Approved
0.7535	Intermediate Similarity	NPD3764	Approved
0.7519	Intermediate Similarity	NPD2182	Approved
0.7519	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6663	Approved
0.7483	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5736	Approved
0.7423	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7458	Discontinued
0.7388	Intermediate Similarity	NPD4198	Discontinued
0.7325	Intermediate Similarity	NPD5761	Phase 2
0.7325	Intermediate Similarity	NPD5760	Phase 2
0.729	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6287	Discontinued
0.7209	Intermediate Similarity	NPD164	Approved
0.7192	Intermediate Similarity	NPD4140	Approved
0.7186	Intermediate Similarity	NPD8368	Discontinued
0.7181	Intermediate Similarity	NPD5408	Approved
0.7181	Intermediate Similarity	NPD5404	Approved
0.7181	Intermediate Similarity	NPD5405	Approved
0.7181	Intermediate Similarity	NPD5406	Approved
0.7176	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1238	Approved
0.716	Intermediate Similarity	NPD8407	Phase 2
0.7133	Intermediate Similarity	NPD2346	Discontinued
0.7132	Intermediate Similarity	NPD1930	Approved
0.7132	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6647	Phase 2
0.7132	Intermediate Similarity	NPD1929	Approved
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7123	Intermediate Similarity	NPD8032	Phase 2
0.7122	Intermediate Similarity	NPD5125	Phase 3
0.7122	Intermediate Similarity	NPD5126	Approved
0.7114	Intermediate Similarity	NPD7305	Phase 1
0.7108	Intermediate Similarity	NPD5844	Phase 1
0.7107	Intermediate Similarity	NPD7819	Suspended
0.7105	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9545	Approved
0.7099	Intermediate Similarity	NPD6685	Approved
0.7093	Intermediate Similarity	NPD8435	Approved
0.7093	Intermediate Similarity	NPD8361	Approved
0.7093	Intermediate Similarity	NPD8360	Approved
0.7083	Intermediate Similarity	NPD6764	Approved
0.7083	Intermediate Similarity	NPD6765	Approved
0.7076	Intermediate Similarity	NPD8434	Phase 2
0.707	Intermediate Similarity	NPD3226	Approved
0.7031	Intermediate Similarity	NPD2066	Phase 3
0.703	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.702	Intermediate Similarity	NPD6005	Phase 3
0.702	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD6002	Phase 3
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5763	Approved
0.702	Intermediate Similarity	NPD6004	Phase 3
0.702	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6085	Phase 2
0.7007	Intermediate Similarity	NPD7714	Approved
0.7007	Intermediate Similarity	NPD7713	Phase 3
0.7007	Intermediate Similarity	NPD7715	Approved
0.7	Intermediate Similarity	NPD3019	Approved
0.7	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.6993	Remote Similarity	NPD3750	Approved
0.6978	Remote Similarity	NPD7009	Phase 2
0.6959	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2935	Discontinued
0.6953	Remote Similarity	NPD7638	Approved
0.6949	Remote Similarity	NPD8485	Approved
0.6947	Remote Similarity	NPD1237	Approved
0.6947	Remote Similarity	NPD5909	Discontinued
0.6939	Remote Similarity	NPD2313	Discontinued
0.6937	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD2532	Approved
0.6919	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6784	Approved
0.6919	Remote Similarity	NPD6785	Approved
0.6914	Remote Similarity	NPD4965	Approved
0.6914	Remote Similarity	NPD4967	Phase 2
0.6914	Remote Similarity	NPD4966	Approved
0.6906	Remote Similarity	NPD7497	Discontinued
0.6899	Remote Similarity	NPD7640	Approved
0.6899	Remote Similarity	NPD7639	Approved
0.6894	Remote Similarity	NPD8455	Phase 2
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3748	Approved
0.6883	Remote Similarity	NPD4110	Phase 3
0.6883	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2932	Approved
0.6879	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD1283	Approved
0.6875	Remote Similarity	NPD7411	Suspended
0.6875	Remote Similarity	NPD1876	Approved
0.687	Remote Similarity	NPD5765	Approved
0.6867	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6010	Discontinued
0.6853	Remote Similarity	NPD1608	Approved
0.6852	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2979	Phase 3
0.6845	Remote Similarity	NPD7177	Discontinued
0.6839	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3023	Approved
0.6831	Remote Similarity	NPD3026	Approved
0.6828	Remote Similarity	NPD1470	Approved
0.6821	Remote Similarity	NPD7097	Phase 1
0.6818	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2067	Discontinued
0.6813	Remote Similarity	NPD4380	Phase 2
0.6813	Remote Similarity	NPD6599	Discontinued
0.6812	Remote Similarity	NPD690	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3025	Approved
0.6809	Remote Similarity	NPD3024	Approved
0.68	Remote Similarity	NPD5735	Approved
0.68	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7473	Discontinued
0.6784	Remote Similarity	NPD7685	Pre-registration
0.6783	Remote Similarity	NPD1201	Approved
0.6781	Remote Similarity	NPD2798	Approved
0.6776	Remote Similarity	NPD7033	Discontinued
0.6768	Remote Similarity	NPD7075	Discontinued
0.6767	Remote Similarity	NPD5048	Discontinued
0.6761	Remote Similarity	NPD3095	Discontinued
0.6753	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6959	Discontinued
0.6746	Remote Similarity	NPD7228	Approved
0.6742	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3091	Approved
0.6736	Remote Similarity	NPD3972	Approved
0.6731	Remote Similarity	NPD6190	Approved
0.6727	Remote Similarity	NPD6234	Discontinued
0.6726	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1693	Approved
0.6715	Remote Similarity	NPD6912	Phase 3
0.6712	Remote Similarity	NPD3094	Phase 2
0.6712	Remote Similarity	NPD2797	Approved
0.6711	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD7028	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
0.6689	Remote Similarity	NPD7055	Discontinued
0.6688	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD6677	Suspended
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1932	Approved
0.6647	Remote Similarity	NPD7199	Phase 2
0.6646	Remote Similarity	NPD5402	Approved
0.6645	Remote Similarity	NPD6353	Approved
0.6644	Remote Similarity	NPD7095	Approved
0.6643	Remote Similarity	NPD17	Approved
0.6643	Remote Similarity	NPD1778	Approved
0.6641	Remote Similarity	NPD1202	Approved
0.6641	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6801	Discontinued

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