NPASS Compound

Structure

NPC173630 OpenBabel07101719122D 27 33 0 0 1 0 0 0 0 0999 V2000 3.3594 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 -1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3594 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3532 -1.2137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5195 1.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0062 -1.2137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5195 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 1.9395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6797 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6797 1.9395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8398 0.4849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8398 2.4244 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9395 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3594 2.9093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 0.4849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5195 2.4244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4547 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 -0.0000 2.9093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 9 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 6 0 0 0 12 21 1 0 0 0 0 13 19 1 6 0 0 0 13 22 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 6 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 6 0 0 0 18 27 1 0 0 0 0 19 20 1 6 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.11
Volume:	342.93
LogP:	1.827
LogD:	1.776
LogS:	-4.281
# Rotatable Bonds:	0
TPSA:	104.21
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	5.385
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.621
MDCK Permeability:	3.2139851100509986e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.402

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.88
Plasma Protein Binding (PPB):	94.52298736572266%
Volume Distribution (VD):	0.659
Pgp-substrate:	2.6555559635162354%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.304
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.368
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	11.873
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.994
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.73
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.346
Carcinogencity:	0.939
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC173630

Natural Product ID:	NPC173630
*Common Name:**	QCIVQEKYSGBTOX-VLWVFBAFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QCIVQEKYSGBTOX-VLWVFBAFSA-N
Standard InCHI:	InChI=1S/C20H18O7/c21-12-7-8-13(22)19-18(12,27-19)16(23)15-17(24-15)20(19)25-10-5-1-3-9-4-2-6-11(26-20)14(9)10/h1-6,12-13,15-17,21-23H,7-8H2/t12-,13+,15+,16-,17+,18-,19-/m0/s1
SMILES:	c1cc2cccc3c2c(c1)OC1([C@H]2[C@@H]([C@@H]([C@@]45[C@H](CC[C@H]([C@@]14O5)O)O)O)O2)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342643
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]

☑ 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	6
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[529637]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[529637]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[529637]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[529637]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[529637]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[529637]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[529637]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[529637]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[529637]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[529637]

☑ 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 NPC173630 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	526
0.1-0.2	1847
0.2-0.3	4591
0.3-0.4	10315
0.4-0.5	8432
0.5-0.6	5784
0.6-0.7	8958
0.7-0.8	2183
0.8-0.85	43
0.85-0.9	12
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC288531
0.9783	High Similarity	NPC472155
0.9571	High Similarity	NPC472154
0.95	High Similarity	NPC151704
0.9433	High Similarity	NPC271076
0.9296	High Similarity	NPC23807
0.9214	High Similarity	NPC193920
0.8896	High Similarity	NPC74371
0.8896	High Similarity	NPC120677
0.8873	High Similarity	NPC472151
0.8839	High Similarity	NPC75944
0.8786	High Similarity	NPC138940
0.8766	High Similarity	NPC472153
0.8553	High Similarity	NPC20050
0.8553	High Similarity	NPC306267
0.8544	High Similarity	NPC175082
0.8516	High Similarity	NPC472156
0.8511	High Similarity	NPC284232
0.8487	Intermediate Similarity	NPC21902
0.8487	Intermediate Similarity	NPC233467
0.8428	Intermediate Similarity	NPC472150
0.8397	Intermediate Similarity	NPC183402
0.8366	Intermediate Similarity	NPC469944
0.8366	Intermediate Similarity	NPC322899
0.8366	Intermediate Similarity	NPC226108
0.8366	Intermediate Similarity	NPC272552
0.8366	Intermediate Similarity	NPC134911
0.8366	Intermediate Similarity	NPC44192
0.8366	Intermediate Similarity	NPC46283
0.8344	Intermediate Similarity	NPC100936
0.8344	Intermediate Similarity	NPC175976
0.8344	Intermediate Similarity	NPC1253
0.8333	Intermediate Similarity	NPC102280
0.8333	Intermediate Similarity	NPC99515
0.8333	Intermediate Similarity	NPC248053
0.8333	Intermediate Similarity	NPC155564
0.8333	Intermediate Similarity	NPC190714
0.8322	Intermediate Similarity	NPC168579
0.8322	Intermediate Similarity	NPC138227
0.8322	Intermediate Similarity	NPC469313
0.8322	Intermediate Similarity	NPC76176
0.8312	Intermediate Similarity	NPC78809
0.8311	Intermediate Similarity	NPC472353
0.8288	Intermediate Similarity	NPC134260
0.828	Intermediate Similarity	NPC193749
0.8278	Intermediate Similarity	NPC473480
0.8278	Intermediate Similarity	NPC15538
0.8276	Intermediate Similarity	NPC164787
0.8264	Intermediate Similarity	NPC263064
0.8255	Intermediate Similarity	NPC37793
0.8255	Intermediate Similarity	NPC252169
0.8255	Intermediate Similarity	NPC473044
0.8255	Intermediate Similarity	NPC472451
0.8255	Intermediate Similarity	NPC81638
0.8252	Intermediate Similarity	NPC121376
0.8247	Intermediate Similarity	NPC474442
0.8247	Intermediate Similarity	NPC59692
0.8243	Intermediate Similarity	NPC108674
0.8243	Intermediate Similarity	NPC210192
0.8243	Intermediate Similarity	NPC178054
0.8243	Intermediate Similarity	NPC76871
0.8239	Intermediate Similarity	NPC218003
0.8235	Intermediate Similarity	NPC238140
0.8224	Intermediate Similarity	NPC280945
0.8219	Intermediate Similarity	NPC302701
0.8219	Intermediate Similarity	NPC269091
0.8219	Intermediate Similarity	NPC234952
0.8219	Intermediate Similarity	NPC92932
0.8212	Intermediate Similarity	NPC162193
0.8212	Intermediate Similarity	NPC125755
0.8207	Intermediate Similarity	NPC130496
0.8207	Intermediate Similarity	NPC188555
0.82	Intermediate Similarity	NPC473045
0.82	Intermediate Similarity	NPC25292
0.82	Intermediate Similarity	NPC171932
0.82	Intermediate Similarity	NPC28440
0.8194	Intermediate Similarity	NPC26080
0.8194	Intermediate Similarity	NPC165686
0.8194	Intermediate Similarity	NPC85799
0.8194	Intermediate Similarity	NPC303422
0.8188	Intermediate Similarity	NPC186033
0.8188	Intermediate Similarity	NPC475084
0.8188	Intermediate Similarity	NPC60249
0.8176	Intermediate Similarity	NPC109240
0.817	Intermediate Similarity	NPC44452
0.817	Intermediate Similarity	NPC318373
0.817	Intermediate Similarity	NPC321657
0.8163	Intermediate Similarity	NPC87777
0.8163	Intermediate Similarity	NPC262328
0.8158	Intermediate Similarity	NPC236202
0.8158	Intermediate Similarity	NPC99183
0.8158	Intermediate Similarity	NPC108811
0.8158	Intermediate Similarity	NPC202742
0.8158	Intermediate Similarity	NPC18185
0.8158	Intermediate Similarity	NPC263940
0.8158	Intermediate Similarity	NPC58190
0.8158	Intermediate Similarity	NPC294558
0.8158	Intermediate Similarity	NPC262911
0.8158	Intermediate Similarity	NPC474397
0.8158	Intermediate Similarity	NPC204770
0.8158	Intermediate Similarity	NPC82917
0.8158	Intermediate Similarity	NPC227902
0.8158	Intermediate Similarity	NPC170103
0.8158	Intermediate Similarity	NPC70409
0.8151	Intermediate Similarity	NPC79957
0.8151	Intermediate Similarity	NPC151224
0.8151	Intermediate Similarity	NPC238243
0.8151	Intermediate Similarity	NPC61946
0.8148	Intermediate Similarity	NPC103633
0.8146	Intermediate Similarity	NPC161700
0.8146	Intermediate Similarity	NPC277867
0.8146	Intermediate Similarity	NPC475096
0.8138	Intermediate Similarity	NPC215037
0.8138	Intermediate Similarity	NPC115022
0.8138	Intermediate Similarity	NPC294166
0.8137	Intermediate Similarity	NPC11608
0.8137	Intermediate Similarity	NPC297404
0.8133	Intermediate Similarity	NPC173203
0.8133	Intermediate Similarity	NPC163508
0.8129	Intermediate Similarity	NPC325860
0.8125	Intermediate Similarity	NPC475067
0.8121	Intermediate Similarity	NPC100482
0.8121	Intermediate Similarity	NPC277331
0.8121	Intermediate Similarity	NPC471389
0.8121	Intermediate Similarity	NPC469661
0.8117	Intermediate Similarity	NPC182368
0.8117	Intermediate Similarity	NPC145979
0.8117	Intermediate Similarity	NPC469706
0.8117	Intermediate Similarity	NPC9933
0.8117	Intermediate Similarity	NPC214326
0.8117	Intermediate Similarity	NPC158784
0.8117	Intermediate Similarity	NPC260781
0.8117	Intermediate Similarity	NPC218041
0.8117	Intermediate Similarity	NPC225815
0.8117	Intermediate Similarity	NPC469707
0.8117	Intermediate Similarity	NPC185955
0.8112	Intermediate Similarity	NPC97326
0.8108	Intermediate Similarity	NPC471388
0.8108	Intermediate Similarity	NPC183781
0.8108	Intermediate Similarity	NPC292487
0.8108	Intermediate Similarity	NPC32630
0.8105	Intermediate Similarity	NPC329836
0.8105	Intermediate Similarity	NPC227516
0.8105	Intermediate Similarity	NPC473876
0.8105	Intermediate Similarity	NPC20757
0.8105	Intermediate Similarity	NPC270751
0.8101	Intermediate Similarity	NPC147743
0.8101	Intermediate Similarity	NPC4809
0.8101	Intermediate Similarity	NPC73517
0.8095	Intermediate Similarity	NPC242028
0.8095	Intermediate Similarity	NPC16435
0.8095	Intermediate Similarity	NPC3293
0.8095	Intermediate Similarity	NPC227503
0.8095	Intermediate Similarity	NPC104167
0.8095	Intermediate Similarity	NPC475628
0.8095	Intermediate Similarity	NPC25695
0.8095	Intermediate Similarity	NPC172818
0.8095	Intermediate Similarity	NPC138350
0.8095	Intermediate Similarity	NPC230734
0.8095	Intermediate Similarity	NPC474639
0.8095	Intermediate Similarity	NPC165482
0.8095	Intermediate Similarity	NPC472800
0.8095	Intermediate Similarity	NPC203230
0.8095	Intermediate Similarity	NPC197723
0.8095	Intermediate Similarity	NPC40664
0.8095	Intermediate Similarity	NPC306441
0.8092	Intermediate Similarity	NPC96576
0.8092	Intermediate Similarity	NPC233980
0.8092	Intermediate Similarity	NPC215678
0.8092	Intermediate Similarity	NPC274454
0.8082	Intermediate Similarity	NPC476411
0.8082	Intermediate Similarity	NPC187194
0.8079	Intermediate Similarity	NPC15659
0.8079	Intermediate Similarity	NPC473108
0.8079	Intermediate Similarity	NPC50250
0.8079	Intermediate Similarity	NPC304894
0.8069	Intermediate Similarity	NPC185604
0.8069	Intermediate Similarity	NPC61477
0.8069	Intermediate Similarity	NPC261619
0.8069	Intermediate Similarity	NPC219876
0.8069	Intermediate Similarity	NPC15658
0.8069	Intermediate Similarity	NPC78770
0.8069	Intermediate Similarity	NPC126029
0.8067	Intermediate Similarity	NPC469559
0.8067	Intermediate Similarity	NPC174522
0.8067	Intermediate Similarity	NPC189115
0.8065	Intermediate Similarity	NPC473621
0.8065	Intermediate Similarity	NPC259707
0.8065	Intermediate Similarity	NPC471403
0.8065	Intermediate Similarity	NPC2745
0.8065	Intermediate Similarity	NPC302915
0.8063	Intermediate Similarity	NPC73148
0.8063	Intermediate Similarity	NPC48880
0.8054	Intermediate Similarity	NPC22317
0.8054	Intermediate Similarity	NPC262189
0.8054	Intermediate Similarity	NPC174787
0.8054	Intermediate Similarity	NPC182509
0.8054	Intermediate Similarity	NPC213607
0.8052	Intermediate Similarity	NPC211561
0.8052	Intermediate Similarity	NPC476969

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 NPC173630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	895
0.2-0.3	2000
0.3-0.4	2879
0.4-0.5	1607
0.5-0.6	939
0.6-0.7	385
0.7-0.8	27
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8954	High Similarity	NPD3787	Discontinued
0.8491	Intermediate Similarity	NPD3751	Discontinued
0.8069	Intermediate Similarity	NPD1613	Approved
0.8069	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1091	Approved
0.7881	Intermediate Similarity	NPD6674	Discontinued
0.7793	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4908	Phase 1
0.774	Intermediate Similarity	NPD4625	Phase 3
0.7724	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8455	Phase 2
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3027	Phase 3
0.7603	Intermediate Similarity	NPD2861	Phase 2
0.7595	Intermediate Similarity	NPD1653	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD37	Approved
0.7396	Intermediate Similarity	NPD7228	Approved
0.7394	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD5058	Phase 3
0.7378	Intermediate Similarity	NPD4965	Approved
0.7378	Intermediate Similarity	NPD4966	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD7054	Approved
0.7333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4749	Approved
0.7325	Intermediate Similarity	NPD2677	Approved
0.7321	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7097	Phase 1
0.731	Intermediate Similarity	NPD3705	Approved
0.731	Intermediate Similarity	NPD7472	Approved
0.731	Intermediate Similarity	NPD7074	Phase 3
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6797	Phase 2
0.725	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7225	Intermediate Similarity	NPD7240	Approved
0.7225	Intermediate Similarity	NPD7251	Discontinued
0.7197	Intermediate Similarity	NPD1652	Phase 2
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7808	Phase 3
0.7179	Intermediate Similarity	NPD5763	Approved
0.7179	Intermediate Similarity	NPD5762	Approved
0.7179	Intermediate Similarity	NPD7266	Discontinued
0.7176	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD5125	Phase 3
0.7161	Intermediate Similarity	NPD5960	Phase 3
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7108	Intermediate Similarity	NPD5402	Approved
0.7105	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD290	Approved
0.7101	Intermediate Similarity	NPD6959	Discontinued
0.7097	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4536	Approved
0.7097	Intermediate Similarity	NPD4538	Approved
0.7093	Intermediate Similarity	NPD3818	Discontinued
0.7091	Intermediate Similarity	NPD1934	Approved
0.7078	Intermediate Similarity	NPD5735	Approved
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.7069	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6671	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7052	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5588	Approved
0.7048	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8651	Approved
0.7039	Intermediate Similarity	NPD7095	Approved
0.7037	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6559	Discontinued
0.702	Intermediate Similarity	NPD3018	Phase 2
0.7019	Intermediate Similarity	NPD7212	Phase 2
0.7019	Intermediate Similarity	NPD7213	Phase 3
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6798	Discontinued
0.6989	Remote Similarity	NPD7549	Discontinued
0.6975	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7447	Phase 1
0.697	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2801	Approved
0.6946	Remote Similarity	NPD7819	Suspended
0.6946	Remote Similarity	NPD1465	Phase 2
0.6944	Remote Similarity	NPD709	Approved
0.6944	Remote Similarity	NPD7157	Approved
0.6943	Remote Similarity	NPD2155	Approved
0.6943	Remote Similarity	NPD2156	Approved
0.6943	Remote Similarity	NPD4108	Discontinued
0.6943	Remote Similarity	NPD2154	Approved
0.6939	Remote Similarity	NPD5846	Approved
0.6939	Remote Similarity	NPD6516	Phase 2
0.6937	Remote Similarity	NPD3750	Approved
0.6929	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3817	Phase 2
0.6903	Remote Similarity	NPD2238	Phase 2
0.6903	Remote Similarity	NPD4140	Approved
0.6899	Remote Similarity	NPD6099	Approved
0.6899	Remote Similarity	NPD6100	Approved
0.689	Remote Similarity	NPD5403	Approved
0.6882	Remote Similarity	NPD6780	Approved
0.6882	Remote Similarity	NPD6777	Approved
0.6882	Remote Similarity	NPD6776	Approved
0.6882	Remote Similarity	NPD6781	Approved
0.6882	Remote Similarity	NPD6778	Approved
0.6882	Remote Similarity	NPD6779	Approved
0.6882	Remote Similarity	NPD6782	Approved
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5401	Approved
0.6871	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2983	Phase 2
0.6867	Remote Similarity	NPD2982	Phase 2
0.686	Remote Similarity	NPD7229	Phase 3
0.6859	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7843	Approved
0.6851	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1611	Approved
0.6845	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5494	Approved
0.6835	Remote Similarity	NPD3748	Approved
0.6835	Remote Similarity	NPD7033	Discontinued
0.6833	Remote Similarity	NPD4663	Approved
0.6832	Remote Similarity	NPD7466	Approved
0.6821	Remote Similarity	NPD6696	Suspended
0.6816	Remote Similarity	NPD8054	Approved
0.6816	Remote Similarity	NPD8053	Approved
0.6813	Remote Similarity	NPD2424	Discontinued
0.681	Remote Similarity	NPD1511	Approved
0.6809	Remote Similarity	NPD6823	Phase 2
0.6806	Remote Similarity	NPD5283	Phase 1
0.68	Remote Similarity	NPD2981	Phase 2
0.6795	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3620	Phase 2
0.6795	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6190	Approved
0.6786	Remote Similarity	NPD968	Approved
0.678	Remote Similarity	NPD7007	Discovery
0.6779	Remote Similarity	NPD3496	Discontinued
0.6772	Remote Similarity	NPD7435	Discontinued
0.6765	Remote Similarity	NPD7768	Phase 2
0.6763	Remote Similarity	NPD6232	Discontinued
0.6763	Remote Similarity	NPD3051	Approved
0.6761	Remote Similarity	NPD8156	Discontinued
0.676	Remote Similarity	NPD4578	Approved
0.676	Remote Similarity	NPD4577	Approved
0.6757	Remote Similarity	NPD1357	Approved
0.6755	Remote Similarity	NPD5327	Phase 3
0.6755	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1375	Discontinued
0.675	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7685	Pre-registration
0.6733	Remote Similarity	NPD422	Phase 1
0.6728	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4628	Phase 3
0.6727	Remote Similarity	NPD1512	Approved
0.6726	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3749	Approved
0.6725	Remote Similarity	NPD7075	Discontinued
0.6711	Remote Similarity	NPD3225	Approved
0.6709	Remote Similarity	NPD6353	Approved
0.6709	Remote Similarity	NPD6653	Approved
0.6708	Remote Similarity	NPD1549	Phase 2
0.6707	Remote Similarity	NPD6799	Approved
0.6707	Remote Similarity	NPD4005	Discontinued
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8127	Discontinued
0.6705	Remote Similarity	NPD8252	Approved
0.6705	Remote Similarity	NPD8251	Approved
0.6705	Remote Similarity	NPD8099	Discontinued
0.6703	Remote Similarity	NPD6841	Approved
0.6703	Remote Similarity	NPD6843	Phase 3
0.6703	Remote Similarity	NPD7906	Approved
0.6703	Remote Similarity	NPD6842	Approved
0.6701	Remote Similarity	NPD7783	Phase 2
0.6701	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2231	Phase 2
0.6689	Remote Similarity	NPD2235	Phase 2
0.6687	Remote Similarity	NPD6032	Approved
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7697	Approved
0.6684	Remote Similarity	NPD7696	Phase 3
0.6684	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3882	Suspended

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