NPASS Compound

Structure

CID117027 OpenBabel06191715472D 38 45 0 0 0 0 0 0 0 0999 V2000 0.8166 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8587 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7252 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8166 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8587 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7252 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0495 -0.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9927 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8592 -2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0495 -2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9927 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8592 -0.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9155 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1266 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9932 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9155 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1266 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9932 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8666 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1756 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4543 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4543 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0421 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8666 -2.5691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1756 1.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0421 -0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7331 -3.5201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 9 1 0 0 0 0 2 6 1 0 0 0 0 2 10 2 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 2 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 27 33 1 0 0 0 0 28 30 2 0 0 0 0 28 34 1 0 0 0 0 29 31 1 0 0 0 0 29 35 2 0 0 0 0 30 32 1 0 0 0 0 30 36 1 0 0 0 0 31 37 2 0 0 0 0 32 38 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.14
Volume:	507.688
LogP:	5.793
LogD:	3.702
LogS:	-8.342
# Rotatable Bonds:	3
TPSA:	90.44
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	2.913
Fsp3:	0.0
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:	-5.769
MDCK Permeability:	1.0636172191880178e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	101.47066497802734%
Volume Distribution (VD):	0.443
Pgp-substrate:	0.7279543876647949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.535
CYP2C19-inhibitor:	0.633
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.363
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	0.179
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.724
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.141
Carcinogencity:	0.652
Eye Corrosion:	0.003
Eye Irritation:	0.843
Respiratory Toxicity:	0.371

Download Data

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

Natural Product: NPC117027

Natural Product ID:	NPC117027
*Common Name:**	Bisindigotin
IUPAC Name:	n.a.
Synonyms:	Bisindigotin
Standard InCHIKey:	LZGZSWNCEMPXSX-HYOGKJQXSA-N
Standard InCHI:	InChI=1S/C32H18N4O2/c37-31-19-11-3-7-15-23(19)35-29(31)27-25(17-9-1-5-13-21(17)33-27)26-18-10-2-6-14-22(18)34-28(26)30-32(38)20-12-4-8-16-24(20)36-30/h1-16,33,36H/b30-28-
SMILES:	O=C1c2ccccc2N/C/1=C/1N=c2c(=C1c1c([nH]c3c1cccc3)C1=Nc3c(C1=O)cccc3)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474468
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	800.0	nM	PMID[489810]

☑ 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 NPC117027 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	578
0.1-0.2	4762
0.2-0.3	15111
0.3-0.4	15995
0.4-0.5	2504
0.5-0.6	2054
0.6-0.7	1464
0.7-0.8	199
0.8-0.85	27
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC473666
0.875	High Similarity	NPC471943
0.8497	Intermediate Similarity	NPC284775
0.8398	Intermediate Similarity	NPC304203
0.8287	Intermediate Similarity	NPC476460
0.8246	Intermediate Similarity	NPC115232
0.8218	Intermediate Similarity	NPC252572
0.8132	Intermediate Similarity	NPC324091
0.8125	Intermediate Similarity	NPC151635
0.8098	Intermediate Similarity	NPC326422
0.8023	Intermediate Similarity	NPC214106
0.8011	Intermediate Similarity	NPC133003
0.8	Intermediate Similarity	NPC317701
0.7956	Intermediate Similarity	NPC477003
0.7901	Intermediate Similarity	NPC470205
0.7889	Intermediate Similarity	NPC88110
0.7849	Intermediate Similarity	NPC76982
0.7772	Intermediate Similarity	NPC141612
0.7772	Intermediate Similarity	NPC17273
0.7772	Intermediate Similarity	NPC135601
0.776	Intermediate Similarity	NPC21429
0.7747	Intermediate Similarity	NPC191415
0.7677	Intermediate Similarity	NPC470702
0.7677	Intermediate Similarity	NPC473218
0.7638	Intermediate Similarity	NPC470703
0.7611	Intermediate Similarity	NPC161861
0.7571	Intermediate Similarity	NPC8104
0.7539	Intermediate Similarity	NPC79356
0.7539	Intermediate Similarity	NPC102592
0.7528	Intermediate Similarity	NPC42372
0.7528	Intermediate Similarity	NPC71132
0.7515	Intermediate Similarity	NPC136002
0.7514	Intermediate Similarity	NPC102755
0.75	Intermediate Similarity	NPC473930
0.75	Intermediate Similarity	NPC167710
0.7474	Intermediate Similarity	NPC47190
0.7472	Intermediate Similarity	NPC21174
0.7472	Intermediate Similarity	NPC271797
0.7471	Intermediate Similarity	NPC200743
0.7461	Intermediate Similarity	NPC195457
0.7448	Intermediate Similarity	NPC472293
0.7433	Intermediate Similarity	NPC308931
0.7433	Intermediate Similarity	NPC99939
0.7423	Intermediate Similarity	NPC477004
0.7409	Intermediate Similarity	NPC227582
0.7407	Intermediate Similarity	NPC209389
0.7387	Intermediate Similarity	NPC116555
0.7385	Intermediate Similarity	NPC252338
0.7382	Intermediate Similarity	NPC272458
0.7382	Intermediate Similarity	NPC472292
0.7377	Intermediate Similarity	NPC293216
0.7371	Intermediate Similarity	NPC295021
0.7363	Intermediate Similarity	NPC6982
0.7353	Intermediate Similarity	NPC267811
0.7347	Intermediate Similarity	NPC471944
0.7346	Intermediate Similarity	NPC250361
0.7344	Intermediate Similarity	NPC269886
0.7344	Intermediate Similarity	NPC472210
0.7344	Intermediate Similarity	NPC247735
0.7344	Intermediate Similarity	NPC81802
0.7344	Intermediate Similarity	NPC472295
0.7337	Intermediate Similarity	NPC471574
0.7333	Intermediate Similarity	NPC74413
0.7333	Intermediate Similarity	NPC472296
0.7333	Intermediate Similarity	NPC472297
0.7333	Intermediate Similarity	NPC475450
0.7316	Intermediate Similarity	NPC321708
0.7316	Intermediate Similarity	NPC221873
0.7282	Intermediate Similarity	NPC131887
0.7256	Intermediate Similarity	NPC473762
0.7247	Intermediate Similarity	NPC216643
0.7245	Intermediate Similarity	NPC237414
0.7235	Intermediate Similarity	NPC312092
0.7222	Intermediate Similarity	NPC260900
0.722	Intermediate Similarity	NPC322064
0.7219	Intermediate Similarity	NPC477042
0.7219	Intermediate Similarity	NPC91179
0.7216	Intermediate Similarity	NPC195239
0.7216	Intermediate Similarity	NPC157828
0.7212	Intermediate Similarity	NPC473587
0.7207	Intermediate Similarity	NPC135141
0.7207	Intermediate Similarity	NPC92796
0.72	Intermediate Similarity	NPC471191
0.7194	Intermediate Similarity	NPC67288
0.7188	Intermediate Similarity	NPC154339
0.7184	Intermediate Similarity	NPC288838
0.7181	Intermediate Similarity	NPC470677
0.7179	Intermediate Similarity	NPC11445
0.7169	Intermediate Similarity	NPC475428
0.7168	Intermediate Similarity	NPC242556
0.7167	Intermediate Similarity	NPC229173
0.7164	Intermediate Similarity	NPC257175
0.7159	Intermediate Similarity	NPC53947
0.7157	Intermediate Similarity	NPC471194
0.7157	Intermediate Similarity	NPC471193
0.7151	Intermediate Similarity	NPC299594
0.7151	Intermediate Similarity	NPC114033
0.7151	Intermediate Similarity	NPC101130
0.7151	Intermediate Similarity	NPC129412
0.7151	Intermediate Similarity	NPC58268
0.715	Intermediate Similarity	NPC132539
0.7143	Intermediate Similarity	NPC300596
0.7143	Intermediate Similarity	NPC229893
0.7143	Intermediate Similarity	NPC237649
0.7127	Intermediate Similarity	NPC242116
0.7126	Intermediate Similarity	NPC179365
0.7122	Intermediate Similarity	NPC31700
0.712	Intermediate Similarity	NPC99428
0.712	Intermediate Similarity	NPC474897
0.712	Intermediate Similarity	NPC160381
0.7113	Intermediate Similarity	NPC67551
0.7111	Intermediate Similarity	NPC474880
0.7111	Intermediate Similarity	NPC221786
0.7111	Intermediate Similarity	NPC475990
0.7108	Intermediate Similarity	NPC72956
0.7104	Intermediate Similarity	NPC470509
0.7101	Intermediate Similarity	NPC27041
0.7098	Intermediate Similarity	NPC472112
0.7097	Intermediate Similarity	NPC469529
0.7081	Intermediate Similarity	NPC323969
0.7079	Intermediate Similarity	NPC477065
0.7079	Intermediate Similarity	NPC281094
0.7077	Intermediate Similarity	NPC267343
0.7073	Intermediate Similarity	NPC153980
0.7073	Intermediate Similarity	NPC6865
0.7066	Intermediate Similarity	NPC22079
0.7059	Intermediate Similarity	NPC187255
0.7037	Intermediate Similarity	NPC16659
0.7029	Intermediate Similarity	NPC470440
0.7026	Intermediate Similarity	NPC216550
0.7024	Intermediate Similarity	NPC82370
0.7021	Intermediate Similarity	NPC157583
0.7021	Intermediate Similarity	NPC59269
0.702	Intermediate Similarity	NPC34837
0.7017	Intermediate Similarity	NPC474492
0.7016	Intermediate Similarity	NPC472294
0.7016	Intermediate Similarity	NPC110158
0.7011	Intermediate Similarity	NPC114637
0.7006	Intermediate Similarity	NPC124005
0.7006	Intermediate Similarity	NPC37548
0.7005	Intermediate Similarity	NPC472116
0.7	Intermediate Similarity	NPC276657
0.6995	Remote Similarity	NPC17059
0.6995	Remote Similarity	NPC278434
0.6995	Remote Similarity	NPC271734
0.6994	Remote Similarity	NPC284635
0.6994	Remote Similarity	NPC41174
0.699	Remote Similarity	NPC473493
0.6984	Remote Similarity	NPC265710
0.6979	Remote Similarity	NPC473189
0.6974	Remote Similarity	NPC138370
0.6973	Remote Similarity	NPC70949
0.6971	Remote Similarity	NPC36405
0.6971	Remote Similarity	NPC471192
0.697	Remote Similarity	NPC141454
0.6965	Remote Similarity	NPC476073
0.6959	Remote Similarity	NPC195704
0.6959	Remote Similarity	NPC167200
0.6959	Remote Similarity	NPC200397
0.6959	Remote Similarity	NPC138596
0.6959	Remote Similarity	NPC64661
0.6959	Remote Similarity	NPC70155
0.6959	Remote Similarity	NPC292434
0.6959	Remote Similarity	NPC98156
0.6959	Remote Similarity	NPC14448
0.6954	Remote Similarity	NPC181502
0.6954	Remote Similarity	NPC85066
0.6949	Remote Similarity	NPC477134
0.6947	Remote Similarity	NPC73994
0.6947	Remote Similarity	NPC469896
0.6944	Remote Similarity	NPC471458
0.6943	Remote Similarity	NPC94752
0.6939	Remote Similarity	NPC472113
0.6938	Remote Similarity	NPC477715
0.6936	Remote Similarity	NPC88097
0.6931	Remote Similarity	NPC473380
0.6931	Remote Similarity	NPC98715
0.6931	Remote Similarity	NPC145885
0.6931	Remote Similarity	NPC84827
0.6931	Remote Similarity	NPC183662
0.6931	Remote Similarity	NPC217372
0.6931	Remote Similarity	NPC237188
0.6931	Remote Similarity	NPC14113
0.6931	Remote Similarity	NPC15573
0.6931	Remote Similarity	NPC240088
0.6927	Remote Similarity	NPC467063
0.6927	Remote Similarity	NPC284102
0.6923	Remote Similarity	NPC329858
0.6919	Remote Similarity	NPC128244
0.6912	Remote Similarity	NPC267078
0.6912	Remote Similarity	NPC207686
0.6912	Remote Similarity	NPC935
0.6902	Remote Similarity	NPC265100
0.6901	Remote Similarity	NPC198988
0.69	Remote Similarity	NPC220797
0.69	Remote Similarity	NPC474318
0.69	Remote Similarity	NPC268744
0.69	Remote Similarity	NPC153123
0.69	Remote Similarity	NPC201266
0.69	Remote Similarity	NPC475914

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 NPC117027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	744
0.2-0.3	998
0.3-0.4	2179
0.4-0.5	2387
0.5-0.6	1931
0.6-0.7	571
0.7-0.8	38
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
0.7989	Intermediate Similarity	NPD5473	Discontinued
0.7656	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3319	Phase 1
0.7419	Intermediate Similarity	NPD3320	Approved
0.7419	Intermediate Similarity	NPD3318	Approved
0.7394	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4848	Phase 1
0.7356	Intermediate Similarity	NPD3833	Phase 3
0.7356	Intermediate Similarity	NPD3835	Phase 3
0.7327	Intermediate Similarity	NPD7455	Approved
0.7327	Intermediate Similarity	NPD7454	Approved
0.7302	Intermediate Similarity	NPD5809	Phase 3
0.7297	Intermediate Similarity	NPD7865	Approved
0.7228	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4922	Phase 2
0.72	Intermediate Similarity	NPD2008	Discontinued
0.7196	Intermediate Similarity	NPD7564	Discontinued
0.7159	Intermediate Similarity	NPD4462	Approved
0.7159	Intermediate Similarity	NPD4463	Approved
0.7157	Intermediate Similarity	NPD2411	Approved
0.7129	Intermediate Similarity	NPD2509	Approved
0.7129	Intermediate Similarity	NPD2510	Approved
0.7128	Intermediate Similarity	NPD2479	Phase 3
0.7128	Intermediate Similarity	NPD2481	Approved
0.7118	Intermediate Similarity	NPD1262	Discovery
0.7101	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6176	Phase 1
0.7093	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7657	Approved
0.7073	Intermediate Similarity	NPD7656	Approved
0.7065	Intermediate Similarity	NPD5426	Phase 3
0.7062	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3394	Approved
0.7053	Intermediate Similarity	NPD3393	Approved
0.7053	Intermediate Similarity	NPD3389	Approved
0.7044	Intermediate Similarity	NPD2443	Approved
0.7044	Intermediate Similarity	NPD2442	Approved
0.7006	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4880	Discontinued
0.6995	Remote Similarity	NPD4948	Discontinued
0.6985	Remote Similarity	NPD8395	Approved
0.6985	Remote Similarity	NPD8396	Approved
0.6973	Remote Similarity	NPD2844	Phase 3
0.6971	Remote Similarity	NPD5254	Discontinued
0.6963	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7994	Phase 2
0.6954	Remote Similarity	NPD7618	Phase 3
0.6954	Remote Similarity	NPD7619	Phase 3
0.6954	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2213	Approved
0.6923	Remote Similarity	NPD2214	Approved
0.6919	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD8096	Phase 3
0.6908	Remote Similarity	NPD8097	Phase 3
0.69	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6999	Discontinued
0.6897	Remote Similarity	NPD5901	Discontinued
0.6897	Remote Similarity	NPD8114	Approved
0.6897	Remote Similarity	NPD8115	Approved
0.6893	Remote Similarity	NPD4051	Discontinued
0.6888	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6459	Phase 2
0.6869	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7406	Phase 2
0.6868	Remote Similarity	NPD4326	Phase 2
0.6862	Remote Similarity	NPD4524	Discontinued
0.686	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6595	Phase 3
0.6859	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2408	Discontinued
0.6845	Remote Similarity	NPD1573	Approved
0.6845	Remote Similarity	NPD1575	Approved
0.6845	Remote Similarity	NPD1600	Suspended
0.6845	Remote Similarity	NPD7941	Phase 3
0.6837	Remote Similarity	NPD4499	Approved
0.6831	Remote Similarity	NPD1630	Approved
0.6829	Remote Similarity	NPD8322	Phase 2
0.6828	Remote Similarity	NPD7863	Approved
0.6828	Remote Similarity	NPD7864	Approved
0.6825	Remote Similarity	NPD482	Approved
0.6823	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4988	Discontinued
0.6821	Remote Similarity	NPD8431	Approved
0.6818	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6987	Phase 1
0.6814	Remote Similarity	NPD8098	Approved
0.681	Remote Similarity	NPD8160	Phase 2
0.681	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2881	Approved
0.6798	Remote Similarity	NPD2879	Approved
0.6796	Remote Similarity	NPD7665	Phase 2
0.6796	Remote Similarity	NPD7666	Phase 3
0.6793	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7866	Approved
0.6789	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4075	Phase 2
0.6789	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2094	Phase 2
0.6788	Remote Similarity	NPD2092	Phase 2
0.6788	Remote Similarity	NPD2095	Phase 2
0.6778	Remote Similarity	NPD2172	Phase 1
0.6771	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1896	Approved
0.6763	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1592	Phase 3
0.6761	Remote Similarity	NPD1722	Approved
0.6753	Remote Similarity	NPD2091	Phase 2
0.6753	Remote Similarity	NPD2096	Phase 2
0.675	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7817	Phase 1
0.6749	Remote Similarity	NPD7727	Phase 2
0.6748	Remote Similarity	NPD3905	Phase 3
0.6748	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8093	Discontinued
0.6744	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3385	Approved
0.6743	Remote Similarity	NPD786	Approved
0.6737	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3961	Discontinued
0.6735	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD56	Approved
0.6732	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8283	Approved
0.6732	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8282	Approved
0.6731	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6733	Discontinued
0.672	Remote Similarity	NPD1631	Approved
0.672	Remote Similarity	NPD3323	Discontinued
0.6719	Remote Similarity	NPD6448	Phase 1
0.6718	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6664	Approved
0.6715	Remote Similarity	NPD8399	Phase 1
0.6715	Remote Similarity	NPD8423	Phase 2
0.6714	Remote Similarity	NPD8094	Discontinued
0.6714	Remote Similarity	NPD6787	Phase 2
0.6704	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2837	Discontinued
0.6702	Remote Similarity	NPD1343	Approved
0.6702	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5021	Discontinued
0.67	Remote Similarity	NPD4501	Approved
0.67	Remote Similarity	NPD4500	Approved
0.6699	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7001	Phase 3
0.6699	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3868	Phase 1
0.6684	Remote Similarity	NPD6217	Discontinued
0.6684	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2915	Discontinued
0.6683	Remote Similarity	NPD4506	Discontinued
0.6683	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7946	Pre-registration
0.6682	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1871	Approved
0.6667	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6446	Discontinued
0.6648	Remote Similarity	NPD3248	Phase 1
0.6635	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD2880	Discontinued
0.6634	Remote Similarity	NPD5003	Discontinued
0.6632	Remote Similarity	NPD3077	Approved
0.6632	Remote Similarity	NPD3078	Approved
0.6632	Remote Similarity	NPD3076	Approved
0.6632	Remote Similarity	NPD3079	Approved
0.663	Remote Similarity	NPD3100	Discontinued
0.6621	Remote Similarity	NPD7781	Approved
0.6621	Remote Similarity	NPD7780	Approved
0.6619	Remote Similarity	NPD5475	Discontinued
0.6619	Remote Similarity	NPD5416	Discontinued
0.6618	Remote Similarity	NPD4601	Approved
0.6618	Remote Similarity	NPD8403	Phase 1
0.6618	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7957	Phase 1
0.6618	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4600	Approved
0.6617	Remote Similarity	NPD7944	Discontinued
0.6616	Remote Similarity	NPD1534	Approved
0.6612	Remote Similarity	NPD2790	Discontinued
0.6608	Remote Similarity	NPD947	Approved
0.6605	Remote Similarity	NPD6242	Discontinued
0.6592	Remote Similarity	NPD7853	Phase 2
0.6589	Remote Similarity	NPD7878	Phase 2
0.6587	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7869	Discontinued
0.6577	Remote Similarity	NPD8047	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data