NPASS Compound

Structure

CID172687 OpenBabel06191715542D 37 41 0 0 1 0 0 0 0 0999 V2000 0.8974 -2.7623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4432 -3.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6409 4.2299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1877 3.5416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4381 2.3552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9508 1.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2667 -1.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 -0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6931 1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8182 2.5462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0793 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9259 0.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 2.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3856 1.9557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8691 -2.6604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2156 3.4393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2326 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 1.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5389 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2324 1.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5392 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3860 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9257 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 1.4664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8465 0.4887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4049 -0.0121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3862 -1.0246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -0.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8467 -0.5113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0789 1.9560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 1.9551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 31 1 0 0 0 0 22 35 1 0 0 0 0 23 24 2 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 32 1 0 0 0 0 26 37 1 0 0 0 0 27 30 1 0 0 0 0 27 33 2 0 0 0 0 28 35 1 0 0 0 0 29 30 1 1 0 0 0 29 36 1 0 0 0 0 30 34 1 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.21
Volume:	519.821
LogP:	7.667
LogD:	4.596
LogS:	-3.027
# Rotatable Bonds:	4
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.459
Synthetic Accessibility Score:	4.576
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.811
MDCK Permeability:	1.7457708963775076e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.422
20% Bioavailability (F20%):	0.761
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	88.16790008544922%
Volume Distribution (VD):	1.086
Pgp-substrate:	10.984176635742188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.358
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.793
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.812
CYP2C9-substrate:	0.389
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	8.217
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.586
Carcinogencity:	0.832
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC172687

Natural Product ID:	NPC172687
*Common Name:**	Sorocein D
IUPAC Name:	n.a.
Synonyms:	Sorocein D
Standard InCHIKey:	BSEWSLOUHTTXHH-LOYHVIPDSA-N
Standard InCHI:	InChI=1S/C30H32O7/c1-16(2)7-8-18-21(31)10-9-20-26(18)37-30(34)27(33)24-23(36-29(20,30)14-11-17(3)4)15-22-19(25(24)32)12-13-28(5,6)35-22/h7,9-13,15,31-32,34H,8,14H2,1-6H3/t29-,30-/m1/s1
SMILES:	CC(=CC[C@@]12Oc3cc4OC(C)(C)C=Cc4c(c3C(=O)[C@@]2(O)Oc2c1ccc(c2CC=C(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517862
PubChem CID:	44559965
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25003	Sorocea bonplandii	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8038	Pachliopta aristolochiae	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25003	Sorocea bonplandii	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2322	Oryctes nevadensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9402	Morus mongolica	Species	Moraceae	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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	190000.0	nM	PMID[522889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	120000.0	nM	PMID[522889]
NPT27	Others	Unspecified		CC50	=	270000.0	nM	PMID[522889]
NPT27	Others	Unspecified		Ratio	=	1.4	n.a.	PMID[522889]

☑ 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 NPC172687 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	407
0.1-0.2	1531
0.2-0.3	3543
0.3-0.4	9130
0.4-0.5	9452
0.5-0.6	3820
0.6-0.7	5745
0.7-0.8	5300
0.8-0.85	2834
0.85-0.9	862
0.9-0.95	68
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC264932
0.9934	High Similarity	NPC311574
0.9868	High Similarity	NPC210048
0.9868	High Similarity	NPC161650
0.9371	High Similarity	NPC292233
0.9351	High Similarity	NPC476169
0.9286	High Similarity	NPC209760
0.9286	High Similarity	NPC100134
0.9286	High Similarity	NPC311579
0.9286	High Similarity	NPC236756
0.9259	High Similarity	NPC73899
0.9259	High Similarity	NPC147363
0.9259	High Similarity	NPC17105
0.9259	High Similarity	NPC474276
0.9236	High Similarity	NPC306978
0.9226	High Similarity	NPC304207
0.9226	High Similarity	NPC48579
0.9226	High Similarity	NPC217706
0.9226	High Similarity	NPC207809
0.9226	High Similarity	NPC469934
0.9226	High Similarity	NPC259710
0.9221	High Similarity	NPC210597
0.9211	High Similarity	NPC296869
0.9182	High Similarity	NPC66087
0.9182	High Similarity	NPC183672
0.9182	High Similarity	NPC179198
0.9182	High Similarity	NPC278419
0.9161	High Similarity	NPC248793
0.9161	High Similarity	NPC180301
0.9156	High Similarity	NPC471675
0.9156	High Similarity	NPC472636
0.9145	High Similarity	NPC166757
0.9145	High Similarity	NPC14001
0.9119	High Similarity	NPC131745
0.9119	High Similarity	NPC150164
0.9119	High Similarity	NPC93215
0.9103	High Similarity	NPC304745
0.9103	High Similarity	NPC111341
0.9103	High Similarity	NPC471116
0.9097	High Similarity	NPC473996
0.9097	High Similarity	NPC477957
0.9097	High Similarity	NPC476238
0.9097	High Similarity	NPC31627
0.9097	High Similarity	NPC142527
0.9097	High Similarity	NPC138288
0.9097	High Similarity	NPC327269
0.9085	High Similarity	NPC244407
0.9079	High Similarity	NPC220418
0.9079	High Similarity	NPC5820
0.9079	High Similarity	NPC178343
0.9079	High Similarity	NPC306488
0.9079	High Similarity	NPC124729
0.9074	High Similarity	NPC5319
0.9073	High Similarity	NPC9117
0.9073	High Similarity	NPC293053
0.9073	High Similarity	NPC24821
0.9073	High Similarity	NPC219915
0.9073	High Similarity	NPC212932
0.9073	High Similarity	NPC190637
0.9045	High Similarity	NPC20530
0.9045	High Similarity	NPC215917
0.9045	High Similarity	NPC10754
0.9045	High Similarity	NPC146636
0.9038	High Similarity	NPC268193
0.9038	High Similarity	NPC7989
0.9038	High Similarity	NPC223701
0.9038	High Similarity	NPC293286
0.9038	High Similarity	NPC472583
0.9032	High Similarity	NPC262039
0.9032	High Similarity	NPC262038
0.9032	High Similarity	NPC471229
0.9032	High Similarity	NPC471677
0.9032	High Similarity	NPC319910
0.9032	High Similarity	NPC278476
0.9032	High Similarity	NPC254412
0.9032	High Similarity	NPC472580
0.9026	High Similarity	NPC277032
0.902	High Similarity	NPC472918
0.9018	High Similarity	NPC287884
0.9018	High Similarity	NPC8704
0.9013	High Similarity	NPC71210
0.9013	High Similarity	NPC273538
0.9013	High Similarity	NPC216538
0.9013	High Similarity	NPC326500
0.9007	High Similarity	NPC200694
0.9007	High Similarity	NPC473042
0.9006	High Similarity	NPC72016
0.9	High Similarity	NPC259834
0.8988	High Similarity	NPC106700
0.8987	High Similarity	NPC237418
0.8981	High Similarity	NPC477958
0.8981	High Similarity	NPC275575
0.8981	High Similarity	NPC108937
0.8981	High Similarity	NPC279218
0.8974	High Similarity	NPC161881
0.8974	High Similarity	NPC244583
0.8974	High Similarity	NPC150123
0.8974	High Similarity	NPC45934
0.8974	High Similarity	NPC10807
0.8974	High Similarity	NPC35567
0.8974	High Similarity	NPC217149
0.8974	High Similarity	NPC475790
0.8974	High Similarity	NPC285623
0.8974	High Similarity	NPC171651
0.8974	High Similarity	NPC56232
0.8974	High Similarity	NPC243171
0.8974	High Similarity	NPC216035
0.8968	High Similarity	NPC267117
0.8968	High Similarity	NPC471984
0.8968	High Similarity	NPC29777
0.8968	High Similarity	NPC105136
0.8968	High Similarity	NPC471115
0.8968	High Similarity	NPC472421
0.8947	High Similarity	NPC38219
0.8947	High Similarity	NPC158874
0.8944	High Similarity	NPC124155
0.8944	High Similarity	NPC257566
0.894	High Similarity	NPC310128
0.8931	High Similarity	NPC320283
0.8931	High Similarity	NPC472459
0.8931	High Similarity	NPC111929
0.8931	High Similarity	NPC125969
0.8931	High Similarity	NPC470607
0.8931	High Similarity	NPC41121
0.8924	High Similarity	NPC475797
0.8924	High Similarity	NPC109967
0.8924	High Similarity	NPC469936
0.8924	High Similarity	NPC78554
0.8924	High Similarity	NPC474609
0.8924	High Similarity	NPC474738
0.8924	High Similarity	NPC129053
0.8924	High Similarity	NPC321372
0.8917	High Similarity	NPC469405
0.8917	High Similarity	NPC20907
0.8917	High Similarity	NPC88983
0.8917	High Similarity	NPC203080
0.8917	High Similarity	NPC244250
0.891	High Similarity	NPC263384
0.891	High Similarity	NPC472420
0.891	High Similarity	NPC472422
0.891	High Similarity	NPC472423
0.891	High Similarity	NPC471676
0.891	High Similarity	NPC474744
0.891	High Similarity	NPC474772
0.891	High Similarity	NPC474021
0.891	High Similarity	NPC244577
0.891	High Similarity	NPC289774
0.891	High Similarity	NPC81474
0.891	High Similarity	NPC209846
0.891	High Similarity	NPC328740
0.891	High Similarity	NPC477897
0.891	High Similarity	NPC474023
0.8903	High Similarity	NPC472628
0.8903	High Similarity	NPC470461
0.8903	High Similarity	NPC269420
0.8896	High Similarity	NPC473077
0.8896	High Similarity	NPC140120
0.8896	High Similarity	NPC296998
0.8896	High Similarity	NPC283234
0.8889	High Similarity	NPC204088
0.8889	High Similarity	NPC329215
0.8889	High Similarity	NPC259007
0.8882	High Similarity	NPC214236
0.8882	High Similarity	NPC472402
0.8882	High Similarity	NPC78332
0.8882	High Similarity	NPC78803
0.8882	High Similarity	NPC299080
0.8882	High Similarity	NPC282636
0.8882	High Similarity	NPC44947
0.8882	High Similarity	NPC59739
0.8882	High Similarity	NPC294863
0.8882	High Similarity	NPC293852
0.8882	High Similarity	NPC240306
0.8882	High Similarity	NPC62840
0.8882	High Similarity	NPC217083
0.8882	High Similarity	NPC144499
0.8882	High Similarity	NPC266725
0.8882	High Similarity	NPC475106
0.8882	High Similarity	NPC471520
0.8882	High Similarity	NPC219861
0.8875	High Similarity	NPC153342
0.8868	High Similarity	NPC108831
0.8868	High Similarity	NPC135391
0.8868	High Similarity	NPC288084
0.8868	High Similarity	NPC133671
0.8868	High Similarity	NPC77672
0.8868	High Similarity	NPC122809
0.8868	High Similarity	NPC182634
0.8868	High Similarity	NPC282390
0.8868	High Similarity	NPC273843
0.8868	High Similarity	NPC197304
0.8868	High Similarity	NPC78263
0.8868	High Similarity	NPC281137
0.8868	High Similarity	NPC65504
0.8868	High Similarity	NPC54802
0.8868	High Similarity	NPC470606
0.8861	High Similarity	NPC92395
0.8861	High Similarity	NPC133392
0.8861	High Similarity	NPC470681
0.8861	High Similarity	NPC87404

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 NPC172687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	914
0.2-0.3	1627
0.3-0.4	2671
0.4-0.5	1923
0.5-0.6	1067
0.6-0.7	393
0.7-0.8	154
0.8-0.85	37
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9074	High Similarity	NPD7804	Clinical (unspecified phase)
0.9013	High Similarity	NPD4378	Clinical (unspecified phase)
0.8987	High Similarity	NPD7075	Discontinued
0.8917	High Similarity	NPD7096	Clinical (unspecified phase)
0.875	High Similarity	NPD4381	Clinical (unspecified phase)
0.8726	High Similarity	NPD4380	Phase 2
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8616	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD7251	Discontinued
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8521	High Similarity	NPD7808	Phase 3
0.8512	High Similarity	NPD6797	Phase 2
0.8509	High Similarity	NPD8443	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD6799	Approved
0.8457	Intermediate Similarity	NPD3882	Suspended
0.8395	Intermediate Similarity	NPD3817	Phase 2
0.8393	Intermediate Similarity	NPD7054	Approved
0.8385	Intermediate Similarity	NPD1934	Approved
0.8375	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD1511	Approved
0.8343	Intermediate Similarity	NPD7472	Approved
0.8343	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD3749	Approved
0.8258	Intermediate Similarity	NPD1549	Phase 2
0.8246	Intermediate Similarity	NPD6559	Discontinued
0.8205	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD5494	Approved
0.8187	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8153	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD2796	Approved
0.8121	Intermediate Similarity	NPD7768	Phase 2
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5401	Approved
0.8061	Intermediate Similarity	NPD5402	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8036	Intermediate Similarity	NPD6959	Discontinued
0.8034	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1243	Approved
0.7953	Intermediate Similarity	NPD7473	Discontinued
0.7935	Intermediate Similarity	NPD1607	Approved
0.7917	Intermediate Similarity	NPD919	Approved
0.7904	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD920	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7834	Intermediate Similarity	NPD3748	Approved
0.7824	Intermediate Similarity	NPD1247	Approved
0.7803	Intermediate Similarity	NPD3751	Discontinued
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.776	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2344	Approved
0.773	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2799	Discontinued
0.7716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2313	Discontinued
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.7673	Intermediate Similarity	NPD6100	Approved
0.7673	Intermediate Similarity	NPD6099	Approved
0.7672	Intermediate Similarity	NPD7584	Approved
0.767	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2798	Approved
0.763	Intermediate Similarity	NPD3926	Phase 2
0.763	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7435	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD4628	Phase 3
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7546	Intermediate Similarity	NPD2309	Approved
0.7545	Intermediate Similarity	NPD3226	Approved
0.7545	Intermediate Similarity	NPD7458	Discontinued
0.7542	Intermediate Similarity	NPD8312	Approved
0.7542	Intermediate Similarity	NPD8313	Approved
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.753	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD2403	Approved
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7471	Intermediate Similarity	NPD8455	Phase 2
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7455	Intermediate Similarity	NPD7390	Discontinued
0.7452	Intermediate Similarity	NPD3268	Approved
0.7436	Intermediate Similarity	NPD4908	Phase 1
0.7421	Intermediate Similarity	NPD7698	Approved
0.7421	Intermediate Similarity	NPD7697	Approved
0.7421	Intermediate Similarity	NPD7696	Phase 3
0.7414	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7391	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7870	Phase 2
0.7382	Intermediate Similarity	NPD7871	Phase 2
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7874	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD5049	Phase 3
0.7358	Intermediate Similarity	NPD943	Approved
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7355	Intermediate Similarity	NPD1203	Approved
0.7355	Intermediate Similarity	NPD2797	Approved
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7337	Intermediate Similarity	NPD4287	Approved
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2354	Approved
0.7326	Intermediate Similarity	NPD4361	Phase 2
0.7326	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7312	Intermediate Similarity	NPD1933	Approved
0.7303	Intermediate Similarity	NPD7228	Approved
0.7301	Intermediate Similarity	NPD1471	Phase 3
0.7299	Intermediate Similarity	NPD6234	Discontinued
0.7288	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD7095	Approved
0.7278	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7268	Intermediate Similarity	NPD7585	Approved
0.7261	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7245	Intermediate Similarity	NPD7801	Approved
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.7238	Intermediate Similarity	NPD7685	Pre-registration
0.7233	Intermediate Similarity	NPD3764	Approved
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7225	Intermediate Similarity	NPD4288	Approved
0.7216	Intermediate Similarity	NPD7583	Approved
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7209	Intermediate Similarity	NPD37	Approved
0.7208	Intermediate Similarity	NPD422	Phase 1
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD8319	Approved
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7184	Intermediate Similarity	NPD4966	Approved
0.7184	Intermediate Similarity	NPD4967	Phase 2
0.7184	Intermediate Similarity	NPD4965	Approved
0.7179	Intermediate Similarity	NPD3225	Approved
0.7178	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3267	Approved
0.7108	Intermediate Similarity	NPD2654	Approved
0.7099	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6585	Discontinued
0.7091	Intermediate Similarity	NPD2353	Approved
0.7091	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.7051	Intermediate Similarity	NPD1608	Approved
0.7037	Intermediate Similarity	NPD4307	Phase 2

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