NPASS Compound

Structure

NPC474640 OpenBabel07101719522D 24 27 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9081 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4732 0.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3017 -0.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4288 0.7492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0347 -0.9773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8518 -1.6678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -1.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 17 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 6 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.09
Volume:	314.075
LogP:	0.524
LogD:	0.385
LogS:	-3.498
# Rotatable Bonds:	1
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	5.882
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	1.2245013749634381e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.769

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	79.42716217041016%
Volume Distribution (VD):	0.541
Pgp-substrate:	19.637968063354492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	6.298
Half-life (T1/2):	0.703

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.664
AMES Toxicity:	0.85
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.956
Carcinogencity:	0.892
Eye Corrosion:	0.004
Eye Irritation:	0.766
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC474640

Natural Product ID:	NPC474640
*Common Name:**	Epihematoxin
IUPAC Name:	n.a.
Synonyms:	Epihematoxin
Standard InCHIKey:	MAHXCOMHJBHBGO-YNPPLXCJSA-N
Standard InCHI:	InChI=1S/C17H16O7/c1-23-15-16(22)6-8-4-11(19)12(20)5-9(8)17(15)3-2-10(18)13(21)14(17)24-7-16/h2-5,15,19-22H,6-7H2,1H3/t15-,16-,17?/m1/s1
SMILES:	CO[C@@H]1[C@]2(O)COC3=C(C(=O)C=CC13c1c(C2)cc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477781
PubChem CID:	24950019
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32846	heamatoxylon campechianum	Species	n.a.	n.a.	stems	XiShuangBanNa, Yunnan Province, China	2005-Sep	PMID[18610999]

☑ 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	7

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	0.3	%	PMID[510030]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	25.0	%	PMID[510030]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	16.3	%	PMID[510030]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	14.5	%	PMID[510030]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	48.1	%	PMID[510030]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	35.2	%	PMID[510030]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	=	86.1	%	PMID[510030]

☑ 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 NPC474640 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	339
0.1-0.2	1372
0.2-0.3	2870
0.3-0.4	7239
0.4-0.5	10858
0.5-0.6	5664
0.6-0.7	10649
0.7-0.8	3682
0.8-0.85	20
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475757
0.9847	High Similarity	NPC470733
0.9167	High Similarity	NPC470747
0.8403	Intermediate Similarity	NPC476840
0.8403	Intermediate Similarity	NPC476842
0.8288	Intermediate Similarity	NPC26045
0.8286	Intermediate Similarity	NPC59239
0.8273	Intermediate Similarity	NPC99795
0.8264	Intermediate Similarity	NPC155192
0.8264	Intermediate Similarity	NPC144284
0.8264	Intermediate Similarity	NPC271494
0.8264	Intermediate Similarity	NPC473591
0.8243	Intermediate Similarity	NPC470330
0.8227	Intermediate Similarity	NPC474453
0.8219	Intermediate Similarity	NPC204644
0.8219	Intermediate Similarity	NPC235557
0.8214	Intermediate Similarity	NPC78575
0.8194	Intermediate Similarity	NPC76032
0.8194	Intermediate Similarity	NPC132723
0.8194	Intermediate Similarity	NPC182249
0.8169	Intermediate Similarity	NPC311256
0.8125	Intermediate Similarity	NPC471152
0.8108	Intermediate Similarity	NPC307205
0.8108	Intermediate Similarity	NPC476841
0.8108	Intermediate Similarity	NPC476843
0.8099	Intermediate Similarity	NPC4170
0.8088	Intermediate Similarity	NPC471794
0.8085	Intermediate Similarity	NPC312341
0.8079	Intermediate Similarity	NPC241636
0.8079	Intermediate Similarity	NPC470618
0.8079	Intermediate Similarity	NPC470619
0.8079	Intermediate Similarity	NPC280753
0.8079	Intermediate Similarity	NPC208785
0.8079	Intermediate Similarity	NPC145527
0.8079	Intermediate Similarity	NPC44378
0.8074	Intermediate Similarity	NPC470414
0.8067	Intermediate Similarity	NPC473876
0.8067	Intermediate Similarity	NPC476821
0.8054	Intermediate Similarity	NPC233980
0.805	Intermediate Similarity	NPC263212
0.8042	Intermediate Similarity	NPC471942
0.8041	Intermediate Similarity	NPC473845
0.8014	Intermediate Similarity	NPC470616
0.8014	Intermediate Similarity	NPC470617
0.8013	Intermediate Similarity	NPC94781
0.8	Intermediate Similarity	NPC252307
0.8	Intermediate Similarity	NPC245826
0.8	Intermediate Similarity	NPC474178
0.8	Intermediate Similarity	NPC471968
0.8	Intermediate Similarity	NPC126206
0.8	Intermediate Similarity	NPC273798
0.8	Intermediate Similarity	NPC474397
0.7987	Intermediate Similarity	NPC271607
0.7987	Intermediate Similarity	NPC280717
0.7987	Intermediate Similarity	NPC90645
0.7987	Intermediate Similarity	NPC472457
0.7986	Intermediate Similarity	NPC214729
0.7973	Intermediate Similarity	NPC477873
0.7973	Intermediate Similarity	NPC252133
0.7973	Intermediate Similarity	NPC310621
0.7973	Intermediate Similarity	NPC469447
0.7973	Intermediate Similarity	NPC248068
0.7959	Intermediate Similarity	NPC473612
0.7959	Intermediate Similarity	NPC265075
0.7959	Intermediate Similarity	NPC38473
0.7945	Intermediate Similarity	NPC230811
0.7945	Intermediate Similarity	NPC89105
0.7945	Intermediate Similarity	NPC197316
0.7945	Intermediate Similarity	NPC139243
0.7945	Intermediate Similarity	NPC64141
0.7945	Intermediate Similarity	NPC32630
0.7945	Intermediate Similarity	NPC476383
0.7945	Intermediate Similarity	NPC81515
0.7945	Intermediate Similarity	NPC472350
0.7945	Intermediate Similarity	NPC116742
0.7945	Intermediate Similarity	NPC68092
0.7935	Intermediate Similarity	NPC474501
0.7933	Intermediate Similarity	NPC320734
0.7931	Intermediate Similarity	NPC234952
0.7931	Intermediate Similarity	NPC68292
0.7931	Intermediate Similarity	NPC471664
0.7931	Intermediate Similarity	NPC471665
0.7931	Intermediate Similarity	NPC476699
0.7922	Intermediate Similarity	NPC83663
0.7922	Intermediate Similarity	NPC475145
0.7922	Intermediate Similarity	NPC473544
0.7922	Intermediate Similarity	NPC266084
0.7922	Intermediate Similarity	NPC475162
0.7922	Intermediate Similarity	NPC475595
0.7922	Intermediate Similarity	NPC475216
0.7919	Intermediate Similarity	NPC93433
0.7919	Intermediate Similarity	NPC209085
0.7919	Intermediate Similarity	NPC224884
0.7919	Intermediate Similarity	NPC474444
0.7919	Intermediate Similarity	NPC473108
0.7919	Intermediate Similarity	NPC284881
0.7919	Intermediate Similarity	NPC264706
0.7917	Intermediate Similarity	NPC287597
0.7917	Intermediate Similarity	NPC119060
0.7917	Intermediate Similarity	NPC886
0.7917	Intermediate Similarity	NPC237594
0.7917	Intermediate Similarity	NPC135127
0.7917	Intermediate Similarity	NPC34293
0.7917	Intermediate Similarity	NPC476387
0.7917	Intermediate Similarity	NPC249791
0.7908	Intermediate Similarity	NPC2745
0.7905	Intermediate Similarity	NPC35212
0.7905	Intermediate Similarity	NPC67467
0.7902	Intermediate Similarity	NPC165612
0.7895	Intermediate Similarity	NPC292206
0.7895	Intermediate Similarity	NPC44452
0.7895	Intermediate Similarity	NPC46549
0.7895	Intermediate Similarity	NPC264229
0.7895	Intermediate Similarity	NPC132810
0.7891	Intermediate Similarity	NPC322021
0.7891	Intermediate Similarity	NPC473799
0.7891	Intermediate Similarity	NPC475530
0.7883	Intermediate Similarity	NPC147654
0.7881	Intermediate Similarity	NPC30720
0.7877	Intermediate Similarity	NPC78363
0.7877	Intermediate Similarity	NPC260425
0.7871	Intermediate Similarity	NPC268484
0.7867	Intermediate Similarity	NPC235195
0.7867	Intermediate Similarity	NPC272619
0.7867	Intermediate Similarity	NPC286245
0.7867	Intermediate Similarity	NPC469375
0.7867	Intermediate Similarity	NPC294679
0.7867	Intermediate Similarity	NPC29932
0.7867	Intermediate Similarity	NPC163898
0.7867	Intermediate Similarity	NPC8493
0.7867	Intermediate Similarity	NPC144247
0.7867	Intermediate Similarity	NPC53520
0.7867	Intermediate Similarity	NPC145301
0.7867	Intermediate Similarity	NPC19862
0.7863	Intermediate Similarity	NPC470355
0.7862	Intermediate Similarity	NPC151224
0.7862	Intermediate Similarity	NPC476870
0.7862	Intermediate Similarity	NPC103082
0.7857	Intermediate Similarity	NPC205918
0.7857	Intermediate Similarity	NPC473773
0.7857	Intermediate Similarity	NPC157783
0.7857	Intermediate Similarity	NPC475579
0.7852	Intermediate Similarity	NPC86198
0.7847	Intermediate Similarity	NPC155209
0.7847	Intermediate Similarity	NPC168799
0.7843	Intermediate Similarity	NPC120171
0.7843	Intermediate Similarity	NPC158784
0.7843	Intermediate Similarity	NPC195561
0.7842	Intermediate Similarity	NPC474532
0.7842	Intermediate Similarity	NPC265413
0.7842	Intermediate Similarity	NPC10154
0.7842	Intermediate Similarity	NPC469568
0.7838	Intermediate Similarity	NPC35216
0.7838	Intermediate Similarity	NPC47471
0.7838	Intermediate Similarity	NPC471853
0.7838	Intermediate Similarity	NPC476377
0.7838	Intermediate Similarity	NPC224876
0.7838	Intermediate Similarity	NPC83375
0.7838	Intermediate Similarity	NPC476385
0.7838	Intermediate Similarity	NPC134405
0.7832	Intermediate Similarity	NPC277804
0.7832	Intermediate Similarity	NPC198388
0.7829	Intermediate Similarity	NPC127046
0.7829	Intermediate Similarity	NPC32017
0.7829	Intermediate Similarity	NPC96930
0.7823	Intermediate Similarity	NPC328273
0.7823	Intermediate Similarity	NPC321184
0.7823	Intermediate Similarity	NPC205195
0.7823	Intermediate Similarity	NPC184613
0.7823	Intermediate Similarity	NPC321638
0.7823	Intermediate Similarity	NPC171134
0.7817	Intermediate Similarity	NPC86030
0.7817	Intermediate Similarity	NPC184092
0.7817	Intermediate Similarity	NPC5851
0.7817	Intermediate Similarity	NPC30174
0.7815	Intermediate Similarity	NPC268515
0.7815	Intermediate Similarity	NPC84786
0.7815	Intermediate Similarity	NPC40222
0.781	Intermediate Similarity	NPC470849
0.781	Intermediate Similarity	NPC470848
0.7808	Intermediate Similarity	NPC154485
0.7808	Intermediate Similarity	NPC471872
0.7808	Intermediate Similarity	NPC471988
0.7808	Intermediate Similarity	NPC38158
0.7808	Intermediate Similarity	NPC202846
0.7808	Intermediate Similarity	NPC474639
0.7808	Intermediate Similarity	NPC230734
0.7808	Intermediate Similarity	NPC227503
0.7808	Intermediate Similarity	NPC143139
0.7806	Intermediate Similarity	NPC223720
0.7801	Intermediate Similarity	NPC165045
0.7801	Intermediate Similarity	NPC108659
0.7801	Intermediate Similarity	NPC79715
0.7801	Intermediate Similarity	NPC231607
0.7801	Intermediate Similarity	NPC5428
0.7801	Intermediate Similarity	NPC264900
0.7801	Intermediate Similarity	NPC118533
0.7801	Intermediate Similarity	NPC476536
0.7801	Intermediate Similarity	NPC471077
0.78	Intermediate Similarity	NPC50250

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 NPC474640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	832
0.2-0.3	1561
0.3-0.4	2845
0.4-0.5	2024
0.5-0.6	1048
0.6-0.7	519
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7945	Intermediate Similarity	NPD7266	Discontinued
0.7905	Intermediate Similarity	NPD8166	Discontinued
0.766	Intermediate Similarity	NPD3094	Phase 2
0.7616	Intermediate Similarity	NPD6190	Approved
0.7569	Intermediate Similarity	NPD3027	Phase 3
0.7534	Intermediate Similarity	NPD3620	Phase 2
0.7534	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1613	Approved
0.7534	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3092	Approved
0.7468	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3021	Approved
0.7444	Intermediate Similarity	NPD3022	Approved
0.7421	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1934	Approved
0.7357	Intermediate Similarity	NPD2932	Approved
0.7351	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3091	Approved
0.7333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6166	Phase 2
0.731	Intermediate Similarity	NPD5736	Approved
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6674	Discontinued
0.7244	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6234	Discontinued
0.7234	Intermediate Similarity	NPD3019	Approved
0.7222	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5844	Phase 1
0.7162	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7228	Approved
0.7125	Intermediate Similarity	NPD4380	Phase 2
0.7124	Intermediate Similarity	NPD5763	Approved
0.7124	Intermediate Similarity	NPD5762	Approved
0.7117	Intermediate Similarity	NPD3882	Suspended
0.7115	Intermediate Similarity	NPD3300	Phase 2
0.7114	Intermediate Similarity	NPD6663	Approved
0.7113	Intermediate Similarity	NPD3095	Discontinued
0.7107	Intermediate Similarity	NPD1653	Approved
0.7105	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7095	Intermediate Similarity	NPD7095	Approved
0.7095	Intermediate Similarity	NPD4625	Phase 3
0.7093	Intermediate Similarity	NPD7311	Approved
0.7093	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7313	Approved
0.7093	Intermediate Similarity	NPD7310	Approved
0.7093	Intermediate Similarity	NPD7312	Approved
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7069	Intermediate Similarity	NPD8150	Discontinued
0.7052	Intermediate Similarity	NPD7309	Approved
0.7047	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3751	Discontinued
0.7037	Intermediate Similarity	NPD37	Approved
0.7027	Intermediate Similarity	NPD4908	Phase 1
0.7024	Intermediate Similarity	NPD27	Approved
0.7024	Intermediate Similarity	NPD2489	Approved
0.702	Intermediate Similarity	NPD5735	Approved
0.7019	Intermediate Similarity	NPD7028	Phase 2
0.7018	Intermediate Similarity	NPD6797	Phase 2
0.7018	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4965	Approved
0.7012	Intermediate Similarity	NPD4967	Phase 2
0.7012	Intermediate Similarity	NPD4966	Approved
0.6994	Remote Similarity	NPD2801	Approved
0.6993	Remote Similarity	NPD4059	Approved
0.6993	Remote Similarity	NPD4626	Approved
0.6986	Remote Similarity	NPD8651	Approved
0.6981	Remote Similarity	NPD1512	Approved
0.6978	Remote Similarity	NPD2494	Approved
0.6978	Remote Similarity	NPD2493	Approved
0.6977	Remote Similarity	NPD7251	Discontinued
0.697	Remote Similarity	NPD7075	Discontinued
0.6964	Remote Similarity	NPD2970	Approved
0.6964	Remote Similarity	NPD2969	Approved
0.6959	Remote Similarity	NPD7074	Phase 3
0.6957	Remote Similarity	NPD228	Approved
0.6954	Remote Similarity	NPD4140	Approved
0.6954	Remote Similarity	NPD943	Approved
0.6948	Remote Similarity	NPD6099	Approved
0.6948	Remote Similarity	NPD6100	Approved
0.6939	Remote Similarity	NPD1470	Approved
0.6932	Remote Similarity	NPD7906	Approved
0.6923	Remote Similarity	NPD5691	Approved
0.6918	Remote Similarity	NPD4749	Approved
0.691	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD230	Phase 1
0.6905	Remote Similarity	NPD6232	Discontinued
0.6901	Remote Similarity	NPD7054	Approved
0.6901	Remote Similarity	NPD5536	Phase 2
0.6897	Remote Similarity	NPD3705	Approved
0.6897	Remote Similarity	NPD4578	Approved
0.6897	Remote Similarity	NPD1201	Approved
0.6897	Remote Similarity	NPD4577	Approved
0.6892	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1465	Phase 2
0.6886	Remote Similarity	NPD5494	Approved
0.6885	Remote Similarity	NPD3452	Approved
0.6885	Remote Similarity	NPD3450	Approved
0.6882	Remote Similarity	NPD7473	Discontinued
0.6879	Remote Similarity	NPD4198	Discontinued
0.6879	Remote Similarity	NPD3750	Approved
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD4663	Approved
0.6875	Remote Similarity	NPD8434	Phase 2
0.6875	Remote Similarity	NPD5125	Phase 3
0.6871	Remote Similarity	NPD6696	Suspended
0.6865	Remote Similarity	NPD4582	Approved
0.6865	Remote Similarity	NPD4583	Approved
0.686	Remote Similarity	NPD7472	Approved
0.6859	Remote Similarity	NPD2424	Discontinued
0.6857	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5283	Phase 1
0.6855	Remote Similarity	NPD1511	Approved
0.6854	Remote Similarity	NPD2490	Approved
0.6854	Remote Similarity	NPD2488	Approved
0.6848	Remote Similarity	NPD3817	Phase 2
0.6845	Remote Similarity	NPD6959	Discontinued
0.6842	Remote Similarity	NPD3818	Discontinued
0.6839	Remote Similarity	NPD5405	Approved
0.6839	Remote Similarity	NPD5404	Approved
0.6839	Remote Similarity	NPD5406	Approved
0.6839	Remote Similarity	NPD5408	Approved
0.6839	Remote Similarity	NPD7808	Phase 3
0.6839	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3026	Approved
0.6828	Remote Similarity	NPD3023	Approved
0.6824	Remote Similarity	NPD2898	Approved
0.6821	Remote Similarity	NPD3764	Approved
0.6813	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4750	Phase 3
0.6811	Remote Similarity	NPD4002	Approved
0.6811	Remote Similarity	NPD4004	Approved
0.681	Remote Similarity	NPD6599	Discontinued
0.6806	Remote Similarity	NPD3025	Approved
0.6806	Remote Similarity	NPD3024	Approved
0.6805	Remote Similarity	NPD3051	Approved
0.6805	Remote Similarity	NPD3787	Discontinued
0.6803	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5327	Phase 3
0.6797	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3657	Discovery
0.6797	Remote Similarity	NPD5124	Phase 1
0.6788	Remote Similarity	NPD7819	Suspended
0.6786	Remote Similarity	NPD7635	Approved
0.6782	Remote Similarity	NPD7685	Pre-registration
0.6781	Remote Similarity	NPD1610	Phase 2
0.6779	Remote Similarity	NPD4624	Approved
0.6774	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4110	Phase 3
0.677	Remote Similarity	NPD6273	Approved
0.677	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3020	Approved
0.6766	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7157	Approved
0.6758	Remote Similarity	NPD2974	Approved
0.6758	Remote Similarity	NPD2975	Approved
0.6758	Remote Similarity	NPD2973	Approved
0.6753	Remote Similarity	NPD6353	Approved
0.675	Remote Similarity	NPD7390	Discontinued
0.675	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4481	Phase 3
0.6718	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6798	Discontinued
0.671	Remote Similarity	NPD4536	Approved
0.671	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4538	Approved
0.671	Remote Similarity	NPD7097	Phase 1
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8313	Approved
0.6705	Remote Similarity	NPD8312	Approved
0.6705	Remote Similarity	NPD5035	Approved
0.6705	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2629	Approved
0.6688	Remote Similarity	NPD4340	Discontinued
0.6688	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD7236	Approved
0.6686	Remote Similarity	NPD7240	Approved
0.6686	Remote Similarity	NPD6559	Discontinued
0.6686	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5090	Approved
0.6667	Remote Similarity	NPD5089	Approved
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD2860	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data