NPASS Compound

Structure

NPC307466 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 7.8793 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 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 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 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 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 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 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 5.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 9 2 0 0 0 0 3 13 1 0 0 0 0 4 11 2 0 0 0 0 4 16 1 0 0 0 0 5 12 2 0 0 0 0 5 17 1 0 0 0 0 6 14 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 1 0 0 0 11 12 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	305.285
LogP:	2.676
LogD:	3.181
LogS:	-3.983
# Rotatable Bonds:	2
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.886
Synthetic Accessibility Score:	3.048
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.964
MDCK Permeability:	2.0309722458478063e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.167
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	99.23930358886719%
Volume Distribution (VD):	0.736
Pgp-substrate:	1.4517885446548462%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.718
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.374

ADMET: Excretion

Clearance (CL):	17.579
Half-life (T1/2):	0.489

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.548
Rat Oral Acute Toxicity:	0.317
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.943
Carcinogencity:	0.876
Eye Corrosion:	0.003
Eye Irritation:	0.876
Respiratory Toxicity:	0.804

Download Data

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

Natural Product: NPC307466

Natural Product ID:	NPC307466
*Common Name:**	Hildegardiol
IUPAC Name:	(3R)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-methoxy-3,4-dihydro-2H-chromen-6-ol
Synonyms:	hildegardiol
Standard InCHIKey:	MBIKSISXYLIKEM-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-20-15-6-14-9(3-13(15)19)2-10(7-21-14)11-4-16-17(5-12(11)18)23-8-22-16/h3-6,10,18-19H,2,7-8H2,1H3/t10-/m0/s1
SMILES:	COc1cc2OC[C@H](Cc2cc1O)c1cc2OCOc2cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507844
PubChem CID:	11623832
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids

*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
NPO22979	Hildegardia barteri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378378]
NPO22979	Hildegardia barteri	Species	Malvaceae	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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	128.0	ug.mL-1	PMID[542979]
NPT554	Organism	Candida glabrata	Candida glabrata	IC50	>	128.0	ug.mL-1	PMID[542979]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>=	64.0	ug.mL-1	PMID[542979]
NPT554	Organism	Candida glabrata	Candida glabrata	IC50	>=	64.0	ug.mL-1	PMID[542979]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC50	>	128.0	ug.mL-1	PMID[542979]

☑ 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 NPC307466 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	442
0.1-0.2	1775
0.2-0.3	4867
0.3-0.4	11953
0.4-0.5	6119
0.5-0.6	4526
0.6-0.7	6629
0.7-0.8	4831
0.8-0.85	1003
0.85-0.9	455
0.9-0.95	90
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC301961
0.9645	High Similarity	NPC166584
0.9643	High Similarity	NPC226540
0.9565	High Similarity	NPC247291
0.9562	High Similarity	NPC30951
0.9562	High Similarity	NPC6369
0.9507	High Similarity	NPC71726
0.9496	High Similarity	NPC107161
0.9493	High Similarity	NPC284464
0.9433	High Similarity	NPC474749
0.9433	High Similarity	NPC11422
0.9433	High Similarity	NPC42716
0.9433	High Similarity	NPC178014
0.9429	High Similarity	NPC102044
0.9429	High Similarity	NPC47633
0.9429	High Similarity	NPC81638
0.9429	High Similarity	NPC85264
0.942	High Similarity	NPC319647
0.942	High Similarity	NPC25966
0.942	High Similarity	NPC245207
0.942	High Similarity	NPC127218
0.9416	High Similarity	NPC197166
0.9384	High Similarity	NPC159922
0.9375	High Similarity	NPC472709
0.9375	High Similarity	NPC472710
0.9371	High Similarity	NPC175976
0.9366	High Similarity	NPC162193
0.9362	High Similarity	NPC12641
0.9362	High Similarity	NPC280092
0.9362	High Similarity	NPC45257
0.9362	High Similarity	NPC63879
0.9362	High Similarity	NPC93323
0.9353	High Similarity	NPC309124
0.9353	High Similarity	NPC259519
0.9353	High Similarity	NPC254759
0.9353	High Similarity	NPC184797
0.9353	High Similarity	NPC160283
0.9353	High Similarity	NPC27495
0.9348	High Similarity	NPC276490
0.9301	High Similarity	NPC39657
0.9301	High Similarity	NPC227902
0.9286	High Similarity	NPC471389
0.9286	High Similarity	NPC311530
0.9281	High Similarity	NPC236306
0.9281	High Similarity	NPC473739
0.9281	High Similarity	NPC292487
0.9281	High Similarity	NPC292882
0.9281	High Similarity	NPC232164
0.9281	High Similarity	NPC9068
0.9275	High Similarity	NPC270456
0.9275	High Similarity	NPC173660
0.9275	High Similarity	NPC248727
0.9275	High Similarity	NPC162659
0.9275	High Similarity	NPC265433
0.9236	High Similarity	NPC248132
0.9236	High Similarity	NPC130449
0.9231	High Similarity	NPC99515
0.9231	High Similarity	NPC190714
0.9225	High Similarity	NPC473046
0.9225	High Similarity	NPC472712
0.9225	High Similarity	NPC118385
0.9225	High Similarity	NPC472713
0.9225	High Similarity	NPC187774
0.922	High Similarity	NPC80326
0.9214	High Similarity	NPC177868
0.9209	High Similarity	NPC103976
0.9209	High Similarity	NPC326797
0.9209	High Similarity	NPC102904
0.9209	High Similarity	NPC107551
0.9209	High Similarity	NPC474039
0.9209	High Similarity	NPC176051
0.9209	High Similarity	NPC474282
0.9203	High Similarity	NPC195022
0.9172	High Similarity	NPC240521
0.9172	High Similarity	NPC51328
0.9172	High Similarity	NPC286235
0.9172	High Similarity	NPC55158
0.9167	High Similarity	NPC21776
0.9167	High Similarity	NPC16269
0.9167	High Similarity	NPC101376
0.9161	High Similarity	NPC180953
0.9161	High Similarity	NPC475096
0.9161	High Similarity	NPC277867
0.9161	High Similarity	NPC161700
0.9155	High Similarity	NPC474808
0.9155	High Similarity	NPC477616
0.9155	High Similarity	NPC472451
0.9155	High Similarity	NPC252169
0.9149	High Similarity	NPC300798
0.9149	High Similarity	NPC58137
0.9143	High Similarity	NPC70682
0.9143	High Similarity	NPC260741
0.9143	High Similarity	NPC471388
0.913	High Similarity	NPC317380
0.9124	High Similarity	NPC127624
0.911	High Similarity	NPC238140
0.9103	High Similarity	NPC270751
0.9097	High Similarity	NPC125755
0.9091	High Similarity	NPC25292
0.9091	High Similarity	NPC121661
0.9091	High Similarity	NPC73467
0.9091	High Similarity	NPC473045
0.9085	High Similarity	NPC472714
0.9085	High Similarity	NPC191231
0.9085	High Similarity	NPC5262
0.9085	High Similarity	NPC41782
0.9085	High Similarity	NPC174522
0.9085	High Similarity	NPC133934
0.9085	High Similarity	NPC184641
0.9085	High Similarity	NPC184684
0.9085	High Similarity	NPC189115
0.9085	High Similarity	NPC475084
0.9065	High Similarity	NPC470356
0.9065	High Similarity	NPC94750
0.9065	High Similarity	NPC112246
0.9065	High Similarity	NPC474206
0.9065	High Similarity	NPC121812
0.9065	High Similarity	NPC260898
0.9065	High Similarity	NPC134968
0.9065	High Similarity	NPC234333
0.9065	High Similarity	NPC112939
0.9065	High Similarity	NPC47398
0.9058	High Similarity	NPC471391
0.9058	High Similarity	NPC471390
0.9054	High Similarity	NPC78809
0.9034	High Similarity	NPC31325
0.9034	High Similarity	NPC213074
0.9034	High Similarity	NPC114505
0.9034	High Similarity	NPC275284
0.9034	High Similarity	NPC193473
0.9034	High Similarity	NPC224674
0.9034	High Similarity	NPC15956
0.9034	High Similarity	NPC116019
0.9028	High Similarity	NPC197352
0.9028	High Similarity	NPC189239
0.9028	High Similarity	NPC166506
0.9028	High Similarity	NPC205316
0.9028	High Similarity	NPC110763
0.9021	High Similarity	NPC298317
0.9021	High Similarity	NPC37793
0.9021	High Similarity	NPC185071
0.9021	High Similarity	NPC470950
0.9021	High Similarity	NPC12728
0.9021	High Similarity	NPC473044
0.9021	High Similarity	NPC185307
0.9021	High Similarity	NPC255566
0.9014	High Similarity	NPC35216
0.9014	High Similarity	NPC87725
0.9014	High Similarity	NPC263261
0.9014	High Similarity	NPC469661
0.9	High Similarity	NPC16435
0.9	High Similarity	NPC472334
0.9	High Similarity	NPC474639
0.9	High Similarity	NPC472336
0.9	High Similarity	NPC230734
0.9	High Similarity	NPC172818
0.9	High Similarity	NPC227503
0.9	High Similarity	NPC306441
0.9	High Similarity	NPC25695
0.8993	High Similarity	NPC474478
0.8993	High Similarity	NPC106215
0.8986	High Similarity	NPC175067
0.8986	High Similarity	NPC6451
0.8986	High Similarity	NPC204215
0.8986	High Similarity	NPC86655
0.8986	High Similarity	NPC202762
0.898	High Similarity	NPC24425
0.8978	High Similarity	NPC214860
0.8966	High Similarity	NPC33832
0.8966	High Similarity	NPC154971
0.8966	High Similarity	NPC252286
0.8958	High Similarity	NPC470235
0.8958	High Similarity	NPC469313
0.8958	High Similarity	NPC283995
0.8958	High Similarity	NPC129417
0.8958	High Similarity	NPC50250
0.8958	High Similarity	NPC168579
0.8958	High Similarity	NPC138227
0.8958	High Similarity	NPC76176
0.8951	High Similarity	NPC2613
0.8951	High Similarity	NPC204347
0.8951	High Similarity	NPC253878
0.8951	High Similarity	NPC472562
0.8951	High Similarity	NPC475891
0.8951	High Similarity	NPC476356
0.8951	High Similarity	NPC59841
0.8951	High Similarity	NPC469559
0.8944	High Similarity	NPC226547
0.8936	High Similarity	NPC211549
0.8929	High Similarity	NPC61946
0.8929	High Similarity	NPC472337
0.8929	High Similarity	NPC151224
0.8921	High Similarity	NPC168059
0.8921	High Similarity	NPC158331
0.8921	High Similarity	NPC196937
0.8921	High Similarity	NPC11060
0.8921	High Similarity	NPC229442
0.8913	High Similarity	NPC474356
0.8913	High Similarity	NPC45715
0.8913	High Similarity	NPC232275

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 NPC307466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	973
0.2-0.3	1999
0.3-0.4	2749
0.4-0.5	1563
0.5-0.6	862
0.6-0.7	538
0.7-0.8	89
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD1530	Clinical (unspecified phase)
0.8714	High Similarity	NPD1613	Approved
0.8714	High Similarity	NPD1612	Clinical (unspecified phase)
0.8696	High Similarity	NPD1529	Clinical (unspecified phase)
0.85	High Similarity	NPD3027	Phase 3
0.8411	Intermediate Similarity	NPD1653	Approved
0.8397	Intermediate Similarity	NPD6234	Discontinued
0.8298	Intermediate Similarity	NPD4908	Phase 1
0.8227	Intermediate Similarity	NPD2861	Phase 2
0.8194	Intermediate Similarity	NPD37	Approved
0.8188	Intermediate Similarity	NPD1610	Phase 2
0.8182	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7199	Phase 2
0.8153	Intermediate Similarity	NPD4966	Approved
0.8153	Intermediate Similarity	NPD4965	Approved
0.8153	Intermediate Similarity	NPD4967	Phase 2
0.8148	Intermediate Similarity	NPD7228	Approved
0.8121	Intermediate Similarity	NPD6674	Discontinued
0.8075	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD3705	Approved
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.7962	Intermediate Similarity	NPD1934	Approved
0.7943	Intermediate Similarity	NPD4749	Approved
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7911	Intermediate Similarity	NPD2801	Approved
0.7879	Intermediate Similarity	NPD7054	Approved
0.7831	Intermediate Similarity	NPD7472	Approved
0.7812	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1091	Approved
0.7799	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1548	Phase 1
0.774	Intermediate Similarity	NPD4625	Phase 3
0.7702	Intermediate Similarity	NPD3882	Suspended
0.7679	Intermediate Similarity	NPD6797	Phase 2
0.7669	Intermediate Similarity	NPD5494	Approved
0.7633	Intermediate Similarity	NPD7251	Discontinued
0.7633	Intermediate Similarity	NPD7240	Approved
0.7632	Intermediate Similarity	NPD7266	Discontinued
0.7603	Intermediate Similarity	NPD3018	Phase 2
0.759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7808	Phase 3
0.7584	Intermediate Similarity	NPD4060	Phase 1
0.7564	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5844	Phase 1
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5283	Phase 1
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7516	Intermediate Similarity	NPD3382	Approved
0.7516	Intermediate Similarity	NPD3383	Approved
0.7516	Intermediate Similarity	NPD3384	Approved
0.75	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7549	Discontinued
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7467	Intermediate Similarity	NPD3620	Phase 2
0.7467	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1357	Approved
0.7457	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1511	Approved
0.7448	Intermediate Similarity	NPD2983	Phase 2
0.7448	Intermediate Similarity	NPD2982	Phase 2
0.7429	Intermediate Similarity	NPD6671	Approved
0.7423	Intermediate Similarity	NPD3817	Phase 2
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD228	Approved
0.7379	Intermediate Similarity	NPD2981	Phase 2
0.7358	Intermediate Similarity	NPD1512	Approved
0.7358	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD6696	Suspended
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7261	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2978	Approved
0.7256	Intermediate Similarity	NPD2977	Approved
0.7251	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3021	Approved
0.7246	Intermediate Similarity	NPD3022	Approved
0.7237	Intermediate Similarity	NPD1558	Phase 1
0.7222	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1652	Phase 2
0.7192	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7447	Phase 1
0.7179	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4675	Approved
0.7178	Intermediate Similarity	NPD4678	Approved
0.7162	Intermediate Similarity	NPD8651	Approved
0.7161	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5588	Approved
0.716	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7152	Intermediate Similarity	NPD7466	Approved
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7135	Intermediate Similarity	NPD7680	Approved
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7126	Intermediate Similarity	NPD7075	Discontinued
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7125	Intermediate Similarity	NPD7212	Phase 2
0.7125	Intermediate Similarity	NPD7213	Phase 3
0.7119	Intermediate Similarity	NPD4663	Approved
0.7117	Intermediate Similarity	NPD4005	Discontinued
0.7102	Intermediate Similarity	NPD8053	Approved
0.7102	Intermediate Similarity	NPD8054	Approved
0.7097	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4536	Approved
0.7097	Intermediate Similarity	NPD4538	Approved
0.7095	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7089	Intermediate Similarity	NPD5177	Phase 3
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7906	Approved
0.7079	Intermediate Similarity	NPD6841	Approved
0.7079	Intermediate Similarity	NPD6843	Phase 3
0.7079	Intermediate Similarity	NPD6842	Approved
0.7076	Intermediate Similarity	NPD27	Approved
0.7076	Intermediate Similarity	NPD2489	Approved
0.7073	Intermediate Similarity	NPD4380	Phase 2
0.707	Intermediate Similarity	NPD5762	Approved
0.707	Intermediate Similarity	NPD5763	Approved
0.707	Intermediate Similarity	NPD3540	Phase 1
0.707	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7157	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7055	Intermediate Similarity	NPD5125	Phase 3
0.7055	Intermediate Similarity	NPD5126	Approved
0.7051	Intermediate Similarity	NPD4108	Discontinued
0.705	Intermediate Similarity	NPD2684	Approved
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7819	Suspended
0.7045	Intermediate Similarity	NPD7313	Approved
0.7045	Intermediate Similarity	NPD7312	Approved
0.7045	Intermediate Similarity	NPD7311	Approved
0.7045	Intermediate Similarity	NPD4577	Approved
0.7045	Intermediate Similarity	NPD4578	Approved
0.7045	Intermediate Similarity	NPD7310	Approved
0.7044	Intermediate Similarity	NPD3750	Approved
0.7044	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6331	Phase 2
0.7044	Intermediate Similarity	NPD4110	Phase 3
0.7039	Intermediate Similarity	NPD7095	Approved
0.703	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD968	Approved
0.7025	Intermediate Similarity	NPD1549	Phase 2
0.7018	Intermediate Similarity	NPD2970	Approved
0.7018	Intermediate Similarity	NPD2969	Approved
0.7007	Intermediate Similarity	NPD3496	Discontinued
0.7006	Intermediate Similarity	NPD3539	Phase 1
0.7006	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD3454	Phase 3
0.7006	Intermediate Similarity	NPD7309	Approved
0.7	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD7097	Phase 1
0.6975	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7843	Approved
0.6968	Remote Similarity	NPD230	Phase 1
0.6968	Remote Similarity	NPD5735	Approved
0.6959	Remote Similarity	NPD3051	Approved
0.6957	Remote Similarity	NPD7124	Phase 2
0.6954	Remote Similarity	NPD6584	Phase 3
0.6946	Remote Similarity	NPD5929	Approved
0.6944	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5960	Phase 3
0.6918	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6799	Approved
0.6914	Remote Similarity	NPD4357	Discontinued
0.6905	Remote Similarity	NPD2560	Approved
0.6905	Remote Similarity	NPD2563	Approved
0.6901	Remote Similarity	NPD1247	Approved
0.6901	Remote Similarity	NPD6959	Discontinued
0.6899	Remote Similarity	NPD2935	Discontinued
0.6897	Remote Similarity	NPD7340	Approved
0.6894	Remote Similarity	NPD2677	Approved
0.6894	Remote Similarity	NPD6190	Approved
0.6887	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD6111	Discontinued
0.6879	Remote Similarity	NPD4978	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