NPASS Compound

Structure

NPC471735 OpenBabel07101718222D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 3.4641 -3.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 3.4641 -0.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 10 2 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 6 1 6 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 6 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.15
Volume:	336.461
LogP:	3.019
LogD:	1.14
LogS:	-3.053
# Rotatable Bonds:	8
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	3.605
Fsp3:	0.588
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:	-5.56
MDCK Permeability:	1.779162084858399e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.875
Human Intestinal Absorption (HIA):	0.862
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	88.04364776611328%
Volume Distribution (VD):	0.366
Pgp-substrate:	20.933198928833008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	4.437
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.176
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.473
Carcinogencity:	0.819
Eye Corrosion:	0.003
Eye Irritation:	0.176
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC471735

Natural Product ID:	NPC471735
*Common Name:**	(1S,3S)-1,6,8-Trihydroxy-3-(7-Hydroxyheptyl)Isochroman-7-Carboxylic Acid
IUPAC Name:	(1S,3S)-1,6,8-trihydroxy-3-(7-hydroxyheptyl)-3,4-dihydro-1H-isochromene-7-carboxylic acid
Synonyms:
Standard InCHIKey:	XYOMNNRURKEWJB-GTNSWQLSSA-N
Standard InCHI:	InChI=1S/C17H24O7/c18-7-5-3-1-2-4-6-11-8-10-9-12(19)14(16(21)22)15(20)13(10)17(23)24-11/h9,11,17-20,23H,1-8H2,(H,21,22)/t11-,17-/m0/s1
SMILES:	C1C(OC(C2=C(C(=C(C=C21)O)C(=O)O)O)O)CCCCCCCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109316
PubChem CID:	76321221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0000487] Salicylic acid and derivatives

*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
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456578]
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	100.0	ug.mL-1	PMID[545631]

☑ 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 NPC471735 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	343
0.1-0.2	1483
0.2-0.3	3288
0.3-0.4	7802
0.4-0.5	11165
0.5-0.6	4030
0.6-0.7	7211
0.7-0.8	6593
0.8-0.85	601
0.85-0.9	149
0.9-0.95	28
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC471734
0.9712	High Similarity	NPC471733
0.9643	High Similarity	NPC471731
0.9504	High Similarity	NPC159721
0.9437	High Similarity	NPC151607
0.9437	High Similarity	NPC42540
0.9366	High Similarity	NPC472610
0.9362	High Similarity	NPC472604
0.9362	High Similarity	NPC472605
0.9291	High Similarity	NPC472600
0.9291	High Similarity	NPC472601
0.9286	High Similarity	NPC472602
0.9225	High Similarity	NPC472603
0.9172	High Similarity	NPC473023
0.9149	High Similarity	NPC212693
0.9149	High Similarity	NPC94248
0.9143	High Similarity	NPC472599
0.9091	High Similarity	NPC53649
0.9085	High Similarity	NPC88269
0.9078	High Similarity	NPC70380
0.9014	High Similarity	NPC191835
0.9007	High Similarity	NPC158481
0.9007	High Similarity	NPC156967
0.9007	High Similarity	NPC235115
0.8966	High Similarity	NPC469542
0.8958	High Similarity	NPC37530
0.8958	High Similarity	NPC158634
0.8951	High Similarity	NPC32360
0.8951	High Similarity	NPC139634
0.8951	High Similarity	NPC105456
0.8944	High Similarity	NPC194579
0.8897	High Similarity	NPC469579
0.8889	High Similarity	NPC99441
0.8889	High Similarity	NPC155205
0.8889	High Similarity	NPC158472
0.8881	High Similarity	NPC33144
0.8881	High Similarity	NPC478200
0.8873	High Similarity	NPC291454
0.8865	High Similarity	NPC474394
0.8865	High Similarity	NPC475645
0.8851	High Similarity	NPC166583
0.8851	High Similarity	NPC53362
0.8836	High Similarity	NPC51106
0.8836	High Similarity	NPC478202
0.8831	High Similarity	NPC470358
0.8828	High Similarity	NPC1704
0.8828	High Similarity	NPC67650
0.8828	High Similarity	NPC478217
0.8828	High Similarity	NPC313123
0.8819	High Similarity	NPC268052
0.8811	High Similarity	NPC245058
0.8811	High Similarity	NPC71256
0.8808	High Similarity	NPC273483
0.8803	High Similarity	NPC142027
0.8794	High Similarity	NPC153783
0.8784	High Similarity	NPC163846
0.8784	High Similarity	NPC225173
0.8767	High Similarity	NPC474385
0.8767	High Similarity	NPC82913
0.8759	High Similarity	NPC165172
0.8759	High Similarity	NPC168471
0.875	High Similarity	NPC475974
0.875	High Similarity	NPC221104
0.875	High Similarity	NPC472799
0.8742	High Similarity	NPC298778
0.8741	High Similarity	NPC50455
0.8733	High Similarity	NPC233267
0.8733	High Similarity	NPC291049
0.8725	High Similarity	NPC125801
0.8725	High Similarity	NPC8817
0.8723	High Similarity	NPC476389
0.8716	High Similarity	NPC83272
0.8707	High Similarity	NPC472006
0.8701	High Similarity	NPC257309
0.8699	High Similarity	NPC244923
0.8699	High Similarity	NPC472035
0.8699	High Similarity	NPC478201
0.8699	High Similarity	NPC470842
0.869	High Similarity	NPC247409
0.869	High Similarity	NPC275356
0.8681	High Similarity	NPC149372
0.8681	High Similarity	NPC474849
0.8681	High Similarity	NPC261292
0.8681	High Similarity	NPC178467
0.8681	High Similarity	NPC65837
0.8681	High Similarity	NPC474771
0.8681	High Similarity	NPC301915
0.8675	High Similarity	NPC150928
0.8671	High Similarity	NPC290803
0.8671	High Similarity	NPC178851
0.8671	High Similarity	NPC27407
0.8667	High Similarity	NPC105415
0.8667	High Similarity	NPC37139
0.8667	High Similarity	NPC221352
0.8662	High Similarity	NPC37299
0.8662	High Similarity	NPC180261
0.8658	High Similarity	NPC470357
0.8658	High Similarity	NPC470570
0.8652	High Similarity	NPC189823
0.8652	High Similarity	NPC219892
0.8649	High Similarity	NPC277426
0.8649	High Similarity	NPC210425
0.8649	High Similarity	NPC280404
0.8649	High Similarity	NPC86373
0.8634	High Similarity	NPC472054
0.863	High Similarity	NPC64664
0.8627	High Similarity	NPC470102
0.8627	High Similarity	NPC471695
0.8618	High Similarity	NPC70016
0.8618	High Similarity	NPC133856
0.8618	High Similarity	NPC72958
0.8618	High Similarity	NPC232645
0.8618	High Similarity	NPC215921
0.8611	High Similarity	NPC118919
0.8609	High Similarity	NPC247219
0.8609	High Similarity	NPC237440
0.8609	High Similarity	NPC270160
0.8601	High Similarity	NPC175943
0.8591	High Similarity	NPC473692
0.8591	High Similarity	NPC257558
0.8591	High Similarity	NPC34482
0.8591	High Similarity	NPC75694
0.8582	High Similarity	NPC296158
0.858	High Similarity	NPC63105
0.858	High Similarity	NPC474345
0.858	High Similarity	NPC470454
0.858	High Similarity	NPC68381
0.858	High Similarity	NPC199533
0.8571	High Similarity	NPC149533
0.8571	High Similarity	NPC89625
0.8571	High Similarity	NPC149618
0.8571	High Similarity	NPC174599
0.8571	High Similarity	NPC82190
0.8571	High Similarity	NPC475730
0.8571	High Similarity	NPC192219
0.8562	High Similarity	NPC259905
0.8562	High Similarity	NPC217447
0.8562	High Similarity	NPC87708
0.8562	High Similarity	NPC474655
0.8553	High Similarity	NPC158866
0.8553	High Similarity	NPC119929
0.8553	High Similarity	NPC325983
0.8552	High Similarity	NPC135837
0.8543	High Similarity	NPC471641
0.8543	High Similarity	NPC471642
0.8543	High Similarity	NPC240253
0.8543	High Similarity	NPC240622
0.8542	High Similarity	NPC278375
0.8535	High Similarity	NPC69868
0.8533	High Similarity	NPC107625
0.8523	High Similarity	NPC478203
0.8523	High Similarity	NPC210966
0.8523	High Similarity	NPC48762
0.8523	High Similarity	NPC126882
0.8521	High Similarity	NPC214702
0.8521	High Similarity	NPC470831
0.8516	High Similarity	NPC148323
0.8516	High Similarity	NPC283480
0.8514	High Similarity	NPC322112
0.8514	High Similarity	NPC250755
0.8497	Intermediate Similarity	NPC470569
0.8493	Intermediate Similarity	NPC472403
0.8493	Intermediate Similarity	NPC9121
0.8493	Intermediate Similarity	NPC177307
0.8491	Intermediate Similarity	NPC7752
0.8487	Intermediate Similarity	NPC476684
0.8487	Intermediate Similarity	NPC77325
0.8487	Intermediate Similarity	NPC4423
0.8477	Intermediate Similarity	NPC476463
0.8477	Intermediate Similarity	NPC137296
0.8477	Intermediate Similarity	NPC210320
0.8477	Intermediate Similarity	NPC472036
0.8467	Intermediate Similarity	NPC134621
0.8467	Intermediate Similarity	NPC472034
0.8462	Intermediate Similarity	NPC478226
0.8462	Intermediate Similarity	NPC208651
0.8462	Intermediate Similarity	NPC206641
0.8457	Intermediate Similarity	NPC30432
0.8457	Intermediate Similarity	NPC76128
0.8457	Intermediate Similarity	NPC111536
0.8457	Intermediate Similarity	NPC271385
0.8457	Intermediate Similarity	NPC5029
0.8456	Intermediate Similarity	NPC84266
0.8452	Intermediate Similarity	NPC16082
0.8452	Intermediate Similarity	NPC82592
0.8442	Intermediate Similarity	NPC175978
0.8442	Intermediate Similarity	NPC271681
0.8442	Intermediate Similarity	NPC473967
0.8442	Intermediate Similarity	NPC167903
0.8442	Intermediate Similarity	NPC115249
0.8442	Intermediate Similarity	NPC478224
0.8435	Intermediate Similarity	NPC92655
0.8435	Intermediate Similarity	NPC52358
0.8431	Intermediate Similarity	NPC470568
0.8431	Intermediate Similarity	NPC472891
0.8431	Intermediate Similarity	NPC202595
0.8431	Intermediate Similarity	NPC179178
0.8431	Intermediate Similarity	NPC469619
0.8431	Intermediate Similarity	NPC56204
0.8431	Intermediate Similarity	NPC469670

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 NPC471735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	932
0.2-0.3	1802
0.3-0.4	2654
0.4-0.5	1887
0.5-0.6	1110
0.6-0.7	315
0.7-0.8	144
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8591	High Similarity	NPD2534	Approved
0.8591	High Similarity	NPD2533	Approved
0.8591	High Similarity	NPD2532	Approved
0.8435	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7819	Suspended
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.8072	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD5711	Approved
0.8025	Intermediate Similarity	NPD5710	Approved
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4380	Phase 2
0.7933	Intermediate Similarity	NPD5404	Approved
0.7933	Intermediate Similarity	NPD5406	Approved
0.7933	Intermediate Similarity	NPD5405	Approved
0.7933	Intermediate Similarity	NPD5408	Approved
0.7925	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5844	Phase 1
0.7888	Intermediate Similarity	NPD7075	Discontinued
0.7881	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7473	Discontinued
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1549	Phase 2
0.7815	Intermediate Similarity	NPD1551	Phase 2
0.7815	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7390	Discontinued
0.7799	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7764	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1510	Phase 2
0.7738	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD1607	Approved
0.7727	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3818	Discontinued
0.7716	Intermediate Similarity	NPD7768	Phase 2
0.7706	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7054	Approved
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD37	Approved
0.764	Intermediate Similarity	NPD6801	Discontinued
0.764	Intermediate Similarity	NPD1934	Approved
0.7633	Intermediate Similarity	NPD7472	Approved
0.7625	Intermediate Similarity	NPD6599	Discontinued
0.7607	Intermediate Similarity	NPD4967	Phase 2
0.7607	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD4966	Approved
0.7607	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1240	Approved
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.7562	Intermediate Similarity	NPD3226	Approved
0.7561	Intermediate Similarity	NPD3749	Approved
0.7544	Intermediate Similarity	NPD7251	Discontinued
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD7228	Approved
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7472	Intermediate Similarity	NPD6535	Approved
0.7472	Intermediate Similarity	NPD6534	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7468	Intermediate Similarity	NPD2796	Approved
0.7467	Intermediate Similarity	NPD3764	Approved
0.7448	Intermediate Similarity	NPD1201	Approved
0.7436	Intermediate Similarity	NPD2800	Approved
0.7432	Intermediate Similarity	NPD7435	Discontinued
0.7429	Intermediate Similarity	NPD8150	Discontinued
0.7421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD9545	Approved
0.7403	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7394	Intermediate Similarity	NPD9493	Approved
0.7391	Intermediate Similarity	NPD8319	Approved
0.7391	Intermediate Similarity	NPD8320	Phase 1
0.7386	Intermediate Similarity	NPD6651	Approved
0.7368	Intermediate Similarity	NPD943	Approved
0.7365	Intermediate Similarity	NPD1470	Approved
0.7365	Intermediate Similarity	NPD1164	Approved
0.7363	Intermediate Similarity	NPD6780	Approved
0.7363	Intermediate Similarity	NPD6776	Approved
0.7363	Intermediate Similarity	NPD6778	Approved
0.7363	Intermediate Similarity	NPD6781	Approved
0.7363	Intermediate Similarity	NPD6777	Approved
0.7363	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD1511	Approved
0.7355	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7700	Phase 2
0.7348	Intermediate Similarity	NPD7699	Phase 2
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD5402	Approved
0.7329	Intermediate Similarity	NPD5403	Approved
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1243	Approved
0.731	Intermediate Similarity	NPD4626	Approved
0.7296	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2799	Discontinued
0.729	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7273	Intermediate Similarity	NPD2801	Approved
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD1512	Approved
0.7262	Intermediate Similarity	NPD5494	Approved
0.7249	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7783	Phase 2
0.7243	Intermediate Similarity	NPD7698	Approved
0.7243	Intermediate Similarity	NPD7696	Phase 3
0.7243	Intermediate Similarity	NPD7697	Approved
0.7241	Intermediate Similarity	NPD5691	Approved
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7237	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6212	Phase 3
0.7222	Intermediate Similarity	NPD920	Approved
0.7222	Intermediate Similarity	NPD6213	Phase 3
0.7222	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7199	Phase 2
0.7208	Intermediate Similarity	NPD5124	Phase 1
0.7208	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5401	Approved
0.7205	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7870	Phase 2
0.7204	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD7874	Approved
0.7196	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6823	Phase 2
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5953	Discontinued
0.7181	Intermediate Similarity	NPD1283	Approved
0.7178	Intermediate Similarity	NPD1653	Approved
0.7171	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD7003	Approved
0.7169	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7240	Approved
0.7133	Intermediate Similarity	NPD1203	Approved
0.7124	Intermediate Similarity	NPD411	Approved
0.7124	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD919	Approved
0.709	Intermediate Similarity	NPD7701	Phase 2
0.7089	Intermediate Similarity	NPD7266	Discontinued
0.7086	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7286	Phase 2
0.7059	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD9269	Phase 2
0.7047	Intermediate Similarity	NPD9717	Approved
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2979	Phase 3
0.7025	Intermediate Similarity	NPD2438	Suspended
0.7019	Intermediate Similarity	NPD6190	Approved
0.7013	Intermediate Similarity	NPD2313	Discontinued
0.7013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7007	Intermediate Similarity	NPD9268	Approved
0.7006	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4749	Approved
0.6993	Remote Similarity	NPD6832	Phase 2
0.6984	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.698	Remote Similarity	NPD422	Phase 1
0.698	Remote Similarity	NPD1281	Approved
0.6979	Remote Similarity	NPD7801	Approved
0.6977	Remote Similarity	NPD3787	Discontinued
0.6977	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD2798	Approved
0.6968	Remote Similarity	NPD6663	Approved
0.6962	Remote Similarity	NPD7033	Discontinued
0.695	Remote Similarity	NPD74	Approved
0.695	Remote Similarity	NPD9266	Approved
0.6946	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5736	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD4288	Approved
0.6914	Remote Similarity	NPD7177	Discontinued
0.6901	Remote Similarity	NPD4750	Phase 3
0.6894	Remote Similarity	NPD6674	Discontinued
0.6889	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4908	Phase 1
0.6879	Remote Similarity	NPD447	Suspended
0.6879	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9267	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