NPASS Compound

Structure

NPC475836 OpenBabel07101718222D 25 29 0 0 1 0 0 0 0 0999 V2000 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6556 -2.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0678 -2.0646 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2543 -3.8917 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 -4.3301 -0.5000 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 -6.2488 -3.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -2.1691 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 -4.3301 -1.5000 0.0000 C 0 0 1 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 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 -6.8366 -4.5962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 -3.6720 -2.9781 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 16 2 0 0 0 0 14 9 1 6 0 0 0 14 19 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 13 1 6 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	339.826
LogP:	4.019
LogD:	3.235
LogS:	-3.937
# Rotatable Bonds:	0
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	3.949
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982
MDCK Permeability:	1.1800667380157392e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.44
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.375
Plasma Protein Binding (PPB):	98.42007446289062%
Volume Distribution (VD):	0.776
Pgp-substrate:	1.5746744871139526%

ADMET: Metabolism

CYP1A2-inhibitor:	0.254
CYP1A2-substrate:	0.614
CYP2C19-inhibitor:	0.491
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.338
CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.326
CYP3A4-substrate:	0.763

ADMET: Excretion

Clearance (CL):	8.671
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.516
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.234
Carcinogencity:	0.734
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.59

Download Data

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

Natural Product: NPC475836

Natural Product ID:	NPC475836
*Common Name:**	Rautandiol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MGXPFABBMNBNJN-CJESRSHOSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-20(2)18(22)6-10-5-13-16(8-15(10)25-20)23-9-14-12-4-3-11(21)7-17(12)24-19(13)14/h3-5,7-8,14,18-19,21-22H,6,9H2,1-2H3/t14-,18?,19-/m0/s1
SMILES:	CC1(C(CC2=CC3=C(C=C2O1)OCC4C3OC5=C4C=CC(=C5)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517074
PubChem CID:	11674519
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[525567]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[525567]

☑ 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 NPC475836 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	1352
0.2-0.3	3510
0.3-0.4	9685
0.4-0.5	9240
0.5-0.6	3830
0.6-0.7	7450
0.7-0.8	5714
0.8-0.85	997
0.85-0.9	379
0.9-0.95	112
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC262585
0.9697	High Similarity	NPC18189
0.9697	High Similarity	NPC20829
0.9695	High Similarity	NPC117048
0.9695	High Similarity	NPC124085
0.9624	High Similarity	NPC474687
0.9618	High Similarity	NPC85435
0.9549	High Similarity	NPC3049
0.9545	High Similarity	NPC97834
0.9545	High Similarity	NPC296915
0.9545	High Similarity	NPC223008
0.9545	High Similarity	NPC225696
0.9545	High Similarity	NPC198154
0.9545	High Similarity	NPC115335
0.9542	High Similarity	NPC13005
0.947	High Similarity	NPC92805
0.9466	High Similarity	NPC196765
0.9466	High Similarity	NPC207892
0.9466	High Similarity	NPC103799
0.9466	High Similarity	NPC300875
0.9466	High Similarity	NPC164574
0.9466	High Similarity	NPC129106
0.9466	High Similarity	NPC280653
0.9466	High Similarity	NPC129784
0.9466	High Similarity	NPC150011
0.9466	High Similarity	NPC206224
0.9466	High Similarity	NPC268917
0.9466	High Similarity	NPC12875
0.9466	High Similarity	NPC228369
0.9466	High Similarity	NPC476166
0.9466	High Similarity	NPC236014
0.9466	High Similarity	NPC17343
0.9466	High Similarity	NPC162801
0.9466	High Similarity	NPC118114
0.9389	High Similarity	NPC27187
0.9389	High Similarity	NPC470225
0.9318	High Similarity	NPC271945
0.9318	High Similarity	NPC118683
0.9318	High Similarity	NPC164804
0.9318	High Similarity	NPC181497
0.9318	High Similarity	NPC68205
0.9318	High Similarity	NPC244888
0.9318	High Similarity	NPC293203
0.9318	High Similarity	NPC211413
0.9286	High Similarity	NPC101376
0.927	High Similarity	NPC5155
0.927	High Similarity	NPC277331
0.927	High Similarity	NPC100482
0.9237	High Similarity	NPC222572
0.9237	High Similarity	NPC274717
0.9237	High Similarity	NPC47283
0.9237	High Similarity	NPC87224
0.9237	High Similarity	NPC53986
0.9237	High Similarity	NPC38664
0.9237	High Similarity	NPC39064
0.9209	High Similarity	NPC475492
0.9203	High Similarity	NPC472353
0.9179	High Similarity	NPC77196
0.9167	High Similarity	NPC93962
0.9149	High Similarity	NPC21776
0.9149	High Similarity	NPC16269
0.9143	High Similarity	NPC469557
0.913	High Similarity	NPC108674
0.913	High Similarity	NPC263261
0.913	High Similarity	NPC87725
0.9111	High Similarity	NPC473107
0.9084	High Similarity	NPC26879
0.9084	High Similarity	NPC283049
0.9084	High Similarity	NPC276212
0.9084	High Similarity	NPC262573
0.9084	High Similarity	NPC471215
0.9084	High Similarity	NPC230479
0.9084	High Similarity	NPC50315
0.9071	High Similarity	NPC280092
0.9071	High Similarity	NPC12641
0.9071	High Similarity	NPC93323
0.9071	High Similarity	NPC473108
0.9071	High Similarity	NPC45257
0.9065	High Similarity	NPC475891
0.9065	High Similarity	NPC204347
0.9065	High Similarity	NPC59841
0.9065	High Similarity	NPC2613
0.9058	High Similarity	NPC309124
0.9058	High Similarity	NPC184797
0.9051	High Similarity	NPC477938
0.9037	High Similarity	NPC215037
0.9023	High Similarity	NPC134360
0.9015	High Similarity	NPC149796
0.9014	High Similarity	NPC474397
0.9008	High Similarity	NPC167571
0.9008	High Similarity	NPC103420
0.9008	High Similarity	NPC207179
0.9008	High Similarity	NPC102540
0.9008	High Similarity	NPC17809
0.9008	High Similarity	NPC188022
0.9008	High Similarity	NPC278552
0.9008	High Similarity	NPC81641
0.9008	High Similarity	NPC285040
0.9	High Similarity	NPC102044
0.9	High Similarity	NPC47633
0.9	High Similarity	NPC85264
0.8986	High Similarity	NPC473739
0.8986	High Similarity	NPC260741
0.8986	High Similarity	NPC236306
0.8986	High Similarity	NPC70682
0.8986	High Similarity	NPC232164
0.8978	High Similarity	NPC470802
0.8978	High Similarity	NPC126101
0.8978	High Similarity	NPC327735
0.8951	High Similarity	NPC20757
0.8951	High Similarity	NPC473876
0.8951	High Similarity	NPC227516
0.8944	High Similarity	NPC260397
0.8944	High Similarity	NPC155564
0.8944	High Similarity	NPC102280
0.8944	High Similarity	NPC248053
0.8936	High Similarity	NPC63879
0.8931	High Similarity	NPC86502
0.8931	High Similarity	NPC294156
0.8931	High Similarity	NPC197351
0.8931	High Similarity	NPC256015
0.8931	High Similarity	NPC106914
0.8931	High Similarity	NPC134195
0.8931	High Similarity	NPC246648
0.8929	High Similarity	NPC84207
0.8929	High Similarity	NPC139976
0.8929	High Similarity	NPC107161
0.8929	High Similarity	NPC49542
0.8929	High Similarity	NPC230718
0.8929	High Similarity	NPC128337
0.8929	High Similarity	NPC5253
0.8921	High Similarity	NPC27495
0.8913	High Similarity	NPC211549
0.8913	High Similarity	NPC262328
0.8913	High Similarity	NPC87777
0.8905	High Similarity	NPC125579
0.8905	High Similarity	NPC61946
0.8905	High Similarity	NPC151224
0.8905	High Similarity	NPC164787
0.8905	High Similarity	NPC473413
0.8889	High Similarity	NPC211561
0.8881	High Similarity	NPC58190
0.8881	High Similarity	NPC18185
0.8881	High Similarity	NPC263940
0.8881	High Similarity	NPC204770
0.8881	High Similarity	NPC236202
0.8881	High Similarity	NPC170103
0.8881	High Similarity	NPC82917
0.8881	High Similarity	NPC108811
0.8881	High Similarity	NPC202742
0.8881	High Similarity	NPC262911
0.8881	High Similarity	NPC294558
0.8881	High Similarity	NPC70409
0.8873	High Similarity	NPC469701
0.8873	High Similarity	NPC181615
0.8865	High Similarity	NPC184607
0.8857	High Similarity	NPC471389
0.8857	High Similarity	NPC35216
0.8857	High Similarity	NPC247291
0.8857	High Similarity	NPC178054
0.8855	High Similarity	NPC38761
0.8855	High Similarity	NPC474160
0.8855	High Similarity	NPC76465
0.8849	High Similarity	NPC32630
0.8849	High Similarity	NPC471388
0.8841	High Similarity	NPC54743
0.8841	High Similarity	NPC306441
0.8841	High Similarity	NPC29799
0.8841	High Similarity	NPC230734
0.8841	High Similarity	NPC263367
0.8841	High Similarity	NPC472800
0.8841	High Similarity	NPC156502
0.8841	High Similarity	NPC270456
0.8841	High Similarity	NPC269091
0.8841	High Similarity	NPC177160
0.8841	High Similarity	NPC162659
0.8841	High Similarity	NPC227503
0.8841	High Similarity	NPC248727
0.8841	High Similarity	NPC474639
0.8841	High Similarity	NPC16435
0.8841	High Similarity	NPC471522
0.8841	High Similarity	NPC10737
0.8841	High Similarity	NPC302701
0.8841	High Similarity	NPC477939
0.8841	High Similarity	NPC209985
0.8841	High Similarity	NPC265433
0.8836	High Similarity	NPC325860
0.8836	High Similarity	NPC160196
0.8832	High Similarity	NPC476615
0.8832	High Similarity	NPC476617
0.8832	High Similarity	NPC476616
0.8828	High Similarity	NPC158784
0.8811	High Similarity	NPC233980
0.8811	High Similarity	NPC96576
0.8803	High Similarity	NPC225445
0.8794	High Similarity	NPC470937
0.8786	High Similarity	NPC259519
0.8786	High Similarity	NPC160283
0.8786	High Similarity	NPC254759
0.8779	High Similarity	NPC100099

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 NPC475836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	824
0.2-0.3	1707
0.3-0.4	2662
0.4-0.5	1756
0.5-0.6	1028
0.6-0.7	686
0.7-0.8	145
0.8-0.85	8
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD4907	Clinical (unspecified phase)
0.8947	High Similarity	NPD4908	Phase 1
0.8702	High Similarity	NPD1610	Phase 2
0.8686	High Similarity	NPD1613	Approved
0.8686	High Similarity	NPD1612	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4625	Phase 3
0.8333	Intermediate Similarity	NPD3027	Phase 3
0.8321	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD2861	Phase 2
0.8273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1548	Phase 1
0.8227	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD5124	Phase 1
0.8162	Intermediate Similarity	NPD4749	Approved
0.8082	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5588	Approved
0.8041	Intermediate Similarity	NPD5058	Phase 3
0.8026	Intermediate Similarity	NPD4380	Phase 2
0.7986	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4538	Approved
0.7986	Intermediate Similarity	NPD4536	Approved
0.7971	Intermediate Similarity	NPD8651	Approved
0.7902	Intermediate Similarity	NPD4060	Phase 1
0.7883	Intermediate Similarity	NPD1091	Approved
0.7871	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5960	Phase 3
0.7785	Intermediate Similarity	NPD7466	Approved
0.777	Intermediate Similarity	NPD2424	Discontinued
0.7748	Intermediate Similarity	NPD7212	Phase 2
0.7748	Intermediate Similarity	NPD7213	Phase 3
0.7736	Intermediate Similarity	NPD5494	Approved
0.773	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7075	Discontinued
0.7722	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1652	Phase 2
0.7718	Intermediate Similarity	NPD6674	Discontinued
0.7697	Intermediate Similarity	NPD7447	Phase 1
0.7697	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1934	Approved
0.7669	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD6166	Phase 2
0.7654	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD8455	Phase 2
0.7639	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD2684	Approved
0.763	Intermediate Similarity	NPD7157	Approved
0.7628	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6355	Discontinued
0.759	Intermediate Similarity	NPD6559	Discontinued
0.7584	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD37	Approved
0.7562	Intermediate Similarity	NPD6234	Discontinued
0.7557	Intermediate Similarity	NPD290	Approved
0.7547	Intermediate Similarity	NPD4965	Approved
0.7547	Intermediate Similarity	NPD4966	Approved
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4967	Phase 2
0.7537	Intermediate Similarity	NPD7843	Approved
0.7533	Intermediate Similarity	NPD1549	Phase 2
0.7518	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD6100	Approved
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.7483	Intermediate Similarity	NPD5735	Approved
0.7482	Intermediate Similarity	NPD5126	Approved
0.7482	Intermediate Similarity	NPD5125	Phase 3
0.747	Intermediate Similarity	NPD7074	Phase 3
0.7469	Intermediate Similarity	NPD6959	Discontinued
0.7469	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6801	Discontinued
0.7468	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5763	Approved
0.7467	Intermediate Similarity	NPD6002	Phase 3
0.7467	Intermediate Similarity	NPD6004	Phase 3
0.7467	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5762	Approved
0.7467	Intermediate Similarity	NPD6005	Phase 3
0.7465	Intermediate Similarity	NPD6696	Suspended
0.745	Intermediate Similarity	NPD7033	Discontinued
0.7438	Intermediate Similarity	NPD7768	Phase 2
0.7436	Intermediate Similarity	NPD1653	Approved
0.7434	Intermediate Similarity	NPD3750	Approved
0.7434	Intermediate Similarity	NPD3892	Phase 2
0.7434	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4535	Phase 3
0.741	Intermediate Similarity	NPD7054	Approved
0.7405	Intermediate Similarity	NPD6072	Discontinued
0.7405	Intermediate Similarity	NPD7411	Suspended
0.7397	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD7472	Approved
0.7357	Intermediate Similarity	NPD5846	Approved
0.7357	Intermediate Similarity	NPD6516	Phase 2
0.7349	Intermediate Similarity	NPD3818	Discontinued
0.7329	Intermediate Similarity	NPD3882	Suspended
0.7321	Intermediate Similarity	NPD6797	Phase 2
0.732	Intermediate Similarity	NPD4628	Phase 3
0.7317	Intermediate Similarity	NPD7229	Phase 3
0.7312	Intermediate Similarity	NPD2801	Approved
0.7312	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD3018	Phase 2
0.7297	Intermediate Similarity	NPD2238	Phase 2
0.7297	Intermediate Similarity	NPD3620	Phase 2
0.7297	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7278	Intermediate Similarity	NPD7240	Approved
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5403	Approved
0.7237	Intermediate Similarity	NPD7266	Discontinued
0.7235	Intermediate Similarity	NPD7808	Phase 3
0.723	Intermediate Similarity	NPD6233	Phase 2
0.7229	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3122	Phase 3
0.7226	Intermediate Similarity	NPD6666	Approved
0.7226	Intermediate Similarity	NPD5283	Phase 1
0.7226	Intermediate Similarity	NPD6667	Approved
0.7219	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7218	Intermediate Similarity	NPD968	Approved
0.7214	Intermediate Similarity	NPD7741	Discontinued
0.7212	Intermediate Similarity	NPD3787	Discontinued
0.7211	Intermediate Similarity	NPD7095	Approved
0.7205	Intermediate Similarity	NPD5929	Approved
0.7181	Intermediate Similarity	NPD4140	Approved
0.7181	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1511	Approved
0.7179	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6799	Approved
0.7179	Intermediate Similarity	NPD7041	Phase 2
0.7178	Intermediate Similarity	NPD3749	Approved
0.7176	Intermediate Similarity	NPD940	Approved
0.7176	Intermediate Similarity	NPD846	Approved
0.7172	Intermediate Similarity	NPD3094	Phase 2
0.7172	Intermediate Similarity	NPD2797	Approved
0.7169	Intermediate Similarity	NPD2970	Approved
0.7169	Intermediate Similarity	NPD2969	Approved
0.7168	Intermediate Similarity	NPD4663	Approved
0.7161	Intermediate Similarity	NPD2677	Approved
0.716	Intermediate Similarity	NPD5402	Approved
0.7153	Intermediate Similarity	NPD6582	Phase 2
0.7153	Intermediate Similarity	NPD5327	Phase 3
0.7153	Intermediate Similarity	NPD2982	Phase 2
0.7153	Intermediate Similarity	NPD2983	Phase 2
0.7153	Intermediate Similarity	NPD6583	Phase 3
0.7152	Intermediate Similarity	NPD2200	Suspended
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4433	Discontinued
0.7143	Intermediate Similarity	NPD5062	Approved
0.7143	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD5061	Approved
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD27	Approved
0.7126	Intermediate Similarity	NPD2489	Approved
0.7125	Intermediate Similarity	NPD6599	Discontinued
0.7123	Intermediate Similarity	NPD3691	Phase 2
0.7123	Intermediate Similarity	NPD6584	Phase 3
0.7123	Intermediate Similarity	NPD3690	Phase 2
0.7108	Intermediate Similarity	NPD3051	Approved
0.7105	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3748	Approved
0.7105	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1465	Phase 2
0.7097	Intermediate Similarity	NPD6331	Phase 2
0.7093	Intermediate Similarity	NPD7310	Approved
0.7093	Intermediate Similarity	NPD7311	Approved
0.7093	Intermediate Similarity	NPD7313	Approved
0.7093	Intermediate Similarity	NPD4577	Approved
0.7093	Intermediate Similarity	NPD7312	Approved
0.7093	Intermediate Similarity	NPD4578	Approved
0.7089	Intermediate Similarity	NPD1512	Approved
0.7086	Intermediate Similarity	NPD6653	Approved
0.7086	Intermediate Similarity	NPD6353	Approved
0.7086	Intermediate Similarity	NPD4097	Suspended
0.7083	Intermediate Similarity	NPD2981	Phase 2
0.7078	Intermediate Similarity	NPD7037	Approved
0.7073	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7340	Approved
0.7067	Intermediate Similarity	NPD1240	Approved
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4750	Phase 3
0.7055	Intermediate Similarity	NPD2415	Discontinued
0.7055	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7309	Approved
0.7047	Intermediate Similarity	NPD3268	Approved
0.7041	Intermediate Similarity	NPD3751	Discontinued
0.7035	Intermediate Similarity	NPD4338	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