NPASS Compound

Structure

CID329215 OpenBabel06191716202D 31 34 0 0 1 0 0 0 0 0999 V2000 0.0850 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 0.9511 -1.6910 0.0000 C 0 0 1 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 3.5491 1.8090 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 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 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 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 1.8171 1.8090 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 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 O 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 -2.0878 1.6750 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 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 17 30 1 0 0 0 0 18 26 2 0 0 0 0 18 31 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 31 1 0 0 0 0 24 30 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.16
Volume:	433.107
LogP:	4.885
LogD:	3.02
LogS:	-4.644
# Rotatable Bonds:	5
TPSA:	100.88
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	3.434
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.88
MDCK Permeability:	2.031645635724999e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.158
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	93.92305755615234%
Volume Distribution (VD):	0.699
Pgp-substrate:	4.14170503616333%

ADMET: Metabolism

CYP1A2-inhibitor:	0.789
CYP1A2-substrate:	0.808
CYP2C19-inhibitor:	0.66
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.618
CYP2D6-inhibitor:	0.166
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	3.189
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.919
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.265
Rat Oral Acute Toxicity:	0.713
Maximum Recommended Daily Dose:	0.226
Skin Sensitization:	0.228
Carcinogencity:	0.532
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.288

Download Data

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

Natural Product: NPC329215

Natural Product ID:	NPC329215
*Common Name:**	Ochrocarpin A
IUPAC Name:	5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-4-phenylfuro[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	LPGFEBXRFJLODR-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C25H24O6/c1-5-13(2)21(27)20-22(28)19-15(14-9-7-6-8-10-14)12-18(26)31-23(19)16-11-17(25(3,4)29)30-24(16)20/h6-13,28-29H,5H2,1-4H3/t13-/m0/s1
SMILES:	CC[C@@H](C(=O)c1c(O)c2c(cc(=O)oc2c2c1oc(c2)C(O)(C)C)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517870
PubChem CID:	44559918
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001389] Neoflavones

*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
NPO369	Ochrocarpos punctatus	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[12141854]
NPO369	Ochrocarpos punctatus	Species	Clusiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	5.2	ug.mL-1	PMID[546224]

☑ 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 NPC329215 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	393
0.1-0.2	1677
0.2-0.3	3884
0.3-0.4	8959
0.4-0.5	9596
0.5-0.6	4280
0.6-0.7	5796
0.7-0.8	4695
0.8-0.85	2601
0.85-0.9	737
0.9-0.95	74
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259007
1.0	High Similarity	NPC204088
0.9809	High Similarity	NPC323137
0.9371	High Similarity	NPC219861
0.9304	High Similarity	NPC244750
0.9264	High Similarity	NPC120220
0.9245	High Similarity	NPC260296
0.9245	High Similarity	NPC115432
0.9236	High Similarity	NPC469934
0.9207	High Similarity	NPC472584
0.9193	High Similarity	NPC155640
0.9193	High Similarity	NPC472581
0.9177	High Similarity	NPC19860
0.9177	High Similarity	NPC469936
0.9177	High Similarity	NPC474609
0.9177	High Similarity	NPC109967
0.9177	High Similarity	NPC129053
0.9177	High Similarity	NPC321372
0.9177	High Similarity	NPC474738
0.9177	High Similarity	NPC475797
0.9177	High Similarity	NPC78554
0.9172	High Similarity	NPC472462
0.9161	High Similarity	NPC37208
0.9161	High Similarity	NPC221868
0.9141	High Similarity	NPC476459
0.9114	High Similarity	NPC108937
0.9114	High Similarity	NPC279218
0.9097	High Similarity	NPC272194
0.9068	High Similarity	NPC14822
0.9068	High Similarity	NPC92589
0.9038	High Similarity	NPC226644
0.9038	High Similarity	NPC37226
0.9006	High Similarity	NPC49009
0.9006	High Similarity	NPC95472
0.9006	High Similarity	NPC169
0.9006	High Similarity	NPC239270
0.9006	High Similarity	NPC303210
0.9	High Similarity	NPC268360
0.9	High Similarity	NPC210048
0.9	High Similarity	NPC65504
0.8987	High Similarity	NPC327269
0.8987	High Similarity	NPC31627
0.8987	High Similarity	NPC476238
0.8987	High Similarity	NPC41326
0.8981	High Similarity	NPC230713
0.8981	High Similarity	NPC78335
0.8968	High Similarity	NPC154217
0.8968	High Similarity	NPC210826
0.8951	High Similarity	NPC74854
0.8951	High Similarity	NPC30655
0.8951	High Similarity	NPC45124
0.8944	High Similarity	NPC264932
0.8944	High Similarity	NPC311574
0.8931	High Similarity	NPC72370
0.8931	High Similarity	NPC213608
0.8931	High Similarity	NPC1477
0.8929	High Similarity	NPC164384
0.8924	High Similarity	NPC170169
0.8924	High Similarity	NPC471675
0.8924	High Similarity	NPC290671
0.8922	High Similarity	NPC261471
0.8917	High Similarity	NPC178202
0.8916	High Similarity	NPC218533
0.8916	High Similarity	NPC78830
0.891	High Similarity	NPC130581
0.891	High Similarity	NPC12148
0.8903	High Similarity	NPC196137
0.8903	High Similarity	NPC326500
0.8903	High Similarity	NPC1886
0.8889	High Similarity	NPC172687
0.8889	High Similarity	NPC220582
0.8889	High Similarity	NPC304839
0.8882	High Similarity	NPC260902
0.8882	High Similarity	NPC161650
0.8882	High Similarity	NPC296957
0.8882	High Similarity	NPC269495
0.8875	High Similarity	NPC476169
0.8875	High Similarity	NPC99199
0.8868	High Similarity	NPC5871
0.8868	High Similarity	NPC210597
0.8868	High Similarity	NPC473996
0.8868	High Similarity	NPC285623
0.8861	High Similarity	NPC472421
0.8854	High Similarity	NPC135325
0.8854	High Similarity	NPC208303
0.8854	High Similarity	NPC161864
0.8846	High Similarity	NPC300267
0.8846	High Similarity	NPC470322
0.8846	High Similarity	NPC124729
0.8846	High Similarity	NPC181388
0.8846	High Similarity	NPC51641
0.8839	High Similarity	NPC212932
0.8839	High Similarity	NPC94794
0.8839	High Similarity	NPC87609
0.8839	High Similarity	NPC293053
0.8839	High Similarity	NPC112791
0.8839	High Similarity	NPC9117
0.8839	High Similarity	NPC188632
0.8839	High Similarity	NPC190637
0.8839	High Similarity	NPC196459
0.8839	High Similarity	NPC225884
0.8839	High Similarity	NPC470296
0.8839	High Similarity	NPC24821
0.8827	High Similarity	NPC40583
0.882	High Similarity	NPC160015
0.882	High Similarity	NPC247677
0.882	High Similarity	NPC13879
0.8812	High Similarity	NPC100134
0.8812	High Similarity	NPC235333
0.8812	High Similarity	NPC209760
0.881	High Similarity	NPC37606
0.881	High Similarity	NPC233956
0.8805	High Similarity	NPC98028
0.8805	High Similarity	NPC471229
0.8805	High Similarity	NPC472636
0.8805	High Similarity	NPC474772
0.8805	High Similarity	NPC472580
0.8805	High Similarity	NPC472423
0.8805	High Similarity	NPC474744
0.8797	High Similarity	NPC296030
0.8797	High Similarity	NPC317492
0.8797	High Similarity	NPC39929
0.8797	High Similarity	NPC469932
0.8795	High Similarity	NPC320789
0.879	High Similarity	NPC249942
0.879	High Similarity	NPC140120
0.879	High Similarity	NPC14001
0.879	High Similarity	NPC166757
0.879	High Similarity	NPC180477
0.879	High Similarity	NPC297886
0.8788	High Similarity	NPC29411
0.8782	High Similarity	NPC469935
0.8782	High Similarity	NPC469953
0.8782	High Similarity	NPC216538
0.8782	High Similarity	NPC178627
0.8782	High Similarity	NPC234629
0.8782	High Similarity	NPC311741
0.8782	High Similarity	NPC273538
0.878	High Similarity	NPC193998
0.878	High Similarity	NPC272722
0.8774	High Similarity	NPC473042
0.8774	High Similarity	NPC313036
0.8774	High Similarity	NPC36181
0.8774	High Similarity	NPC200694
0.8772	High Similarity	NPC97523
0.8765	High Similarity	NPC297807
0.8765	High Similarity	NPC270044
0.8758	High Similarity	NPC148938
0.8758	High Similarity	NPC217706
0.8758	High Similarity	NPC259710
0.8758	High Similarity	NPC207809
0.8758	High Similarity	NPC304207
0.8758	High Similarity	NPC48579
0.8758	High Similarity	NPC471116
0.8758	High Similarity	NPC198490
0.8758	High Similarity	NPC297531
0.8758	High Similarity	NPC473241
0.8758	High Similarity	NPC213936
0.875	High Similarity	NPC477957
0.875	High Similarity	NPC35567
0.875	High Similarity	NPC216035
0.875	High Similarity	NPC171651
0.875	High Similarity	NPC256141
0.875	High Similarity	NPC243171
0.875	High Similarity	NPC217149
0.8742	High Similarity	NPC167576
0.8742	High Similarity	NPC470908
0.8742	High Similarity	NPC191104
0.8742	High Similarity	NPC327059
0.8742	High Similarity	NPC155882
0.8742	High Similarity	NPC474735
0.8742	High Similarity	NPC180351
0.8742	High Similarity	NPC151973
0.8742	High Similarity	NPC321387
0.8742	High Similarity	NPC61258
0.8742	High Similarity	NPC267117
0.8735	High Similarity	NPC53640
0.8734	High Similarity	NPC211811
0.8734	High Similarity	NPC296869
0.8734	High Similarity	NPC469933
0.8734	High Similarity	NPC244407
0.8734	High Similarity	NPC168085
0.8727	High Similarity	NPC109180
0.8726	High Similarity	NPC153758
0.8726	High Similarity	NPC5820
0.8726	High Similarity	NPC220418
0.8726	High Similarity	NPC306488
0.8726	High Similarity	NPC57470
0.8726	High Similarity	NPC178343
0.872	High Similarity	NPC97812
0.8718	High Similarity	NPC17262
0.8718	High Similarity	NPC302181
0.8712	High Similarity	NPC476350
0.8712	High Similarity	NPC476349
0.871	High Similarity	NPC156590
0.871	High Similarity	NPC254010
0.871	High Similarity	NPC147688
0.871	High Similarity	NPC118840
0.871	High Similarity	NPC205006
0.871	High Similarity	NPC64908

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 NPC329215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	942
0.2-0.3	1706
0.3-0.4	2624
0.4-0.5	2023
0.5-0.6	1001
0.6-0.7	330
0.7-0.8	124
0.8-0.85	44
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8782	High Similarity	NPD4378	Clinical (unspecified phase)
0.8765	High Similarity	NPD3749	Approved
0.8765	High Similarity	NPD7075	Discontinued
0.8696	High Similarity	NPD7096	Clinical (unspecified phase)
0.8634	High Similarity	NPD6801	Discontinued
0.8581	High Similarity	NPD1243	Approved
0.8553	High Similarity	NPD920	Approved
0.8544	High Similarity	NPD7410	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6799	Approved
0.8428	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8373	Intermediate Similarity	NPD919	Approved
0.8372	Intermediate Similarity	NPD6559	Discontinued
0.8364	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8303	Intermediate Similarity	NPD3817	Phase 2
0.8302	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6599	Discontinued
0.8261	Intermediate Similarity	NPD1512	Approved
0.8242	Intermediate Similarity	NPD2801	Approved
0.8242	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2344	Approved
0.8204	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8144	Intermediate Similarity	NPD7768	Phase 2
0.814	Intermediate Similarity	NPD3818	Discontinued
0.8137	Intermediate Similarity	NPD1511	Approved
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8129	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8113	Intermediate Similarity	NPD2800	Approved
0.8098	Intermediate Similarity	NPD5403	Approved
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8084	Intermediate Similarity	NPD5402	Approved
0.8084	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD1934	Approved
0.807	Intermediate Similarity	NPD3926	Phase 2
0.8063	Intermediate Similarity	NPD3750	Approved
0.8059	Intermediate Similarity	NPD1247	Approved
0.805	Intermediate Similarity	NPD1549	Phase 2
0.8038	Intermediate Similarity	NPD2796	Approved
0.8036	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2309	Approved
0.8	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2799	Discontinued
0.7975	Intermediate Similarity	NPD5401	Approved
0.7949	Intermediate Similarity	NPD1240	Approved
0.7935	Intermediate Similarity	NPD2313	Discontinued
0.791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7866	Intermediate Similarity	NPD2532	Approved
0.7866	Intermediate Similarity	NPD2534	Approved
0.7866	Intermediate Similarity	NPD2533	Approved
0.7848	Intermediate Similarity	NPD1607	Approved
0.7833	Intermediate Similarity	NPD8434	Phase 2
0.7826	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7811	Intermediate Similarity	NPD1465	Phase 2
0.7797	Intermediate Similarity	NPD6797	Phase 2
0.7797	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD3748	Approved
0.7747	Intermediate Similarity	NPD4287	Approved
0.7746	Intermediate Similarity	NPD6959	Discontinued
0.7709	Intermediate Similarity	NPD7808	Phase 3
0.7702	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD5953	Discontinued
0.7688	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7286	Phase 2
0.7684	Intermediate Similarity	NPD7054	Approved
0.764	Intermediate Similarity	NPD7472	Approved
0.764	Intermediate Similarity	NPD7074	Phase 3
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7613	Intermediate Similarity	NPD1203	Approved
0.7611	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3268	Approved
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD4308	Phase 3
0.7528	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD2797	Approved
0.7484	Intermediate Similarity	NPD3764	Approved
0.7458	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2296	Approved
0.7453	Intermediate Similarity	NPD447	Suspended
0.7439	Intermediate Similarity	NPD1471	Phase 3
0.7423	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD9717	Approved
0.7396	Intermediate Similarity	NPD5049	Phase 3
0.7391	Intermediate Similarity	NPD943	Approved
0.7391	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8312	Approved
0.7377	Intermediate Similarity	NPD8313	Approved
0.7375	Intermediate Similarity	NPD6798	Discontinued
0.7366	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2354	Approved
0.7358	Intermediate Similarity	NPD6832	Phase 2
0.7355	Intermediate Similarity	NPD422	Phase 1
0.7346	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6355	Discontinued
0.7346	Intermediate Similarity	NPD5124	Phase 1
0.7345	Intermediate Similarity	NPD7199	Phase 2
0.7342	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.7318	Intermediate Similarity	NPD2403	Approved
0.7317	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD6808	Phase 2
0.7303	Intermediate Similarity	NPD5711	Approved
0.7284	Intermediate Similarity	NPD4307	Phase 2
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3267	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3266	Approved
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7239	Intermediate Similarity	NPD230	Phase 1
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6234	Discontinued
0.7232	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6233	Phase 2
0.7215	Intermediate Similarity	NPD3225	Approved
0.7207	Intermediate Similarity	NPD3787	Discontinued
0.7202	Intermediate Similarity	NPD7003	Approved
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7178	Intermediate Similarity	NPD4060	Phase 1
0.7173	Intermediate Similarity	NPD4361	Phase 2
0.7173	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD5404	Approved
0.7169	Intermediate Similarity	NPD5408	Approved
0.7169	Intermediate Similarity	NPD5406	Approved
0.7168	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6190	Approved
0.7159	Intermediate Similarity	NPD4288	Approved
0.7157	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1933	Approved
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2353	Approved
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD4360	Phase 2
0.7119	Intermediate Similarity	NPD4965	Approved
0.7119	Intermediate Similarity	NPD4966	Approved
0.7119	Intermediate Similarity	NPD4967	Phase 2
0.7113	Intermediate Similarity	NPD6781	Approved
0.7113	Intermediate Similarity	NPD6778	Approved
0.7113	Intermediate Similarity	NPD6782	Approved
0.7113	Intermediate Similarity	NPD6780	Approved
0.7113	Intermediate Similarity	NPD6777	Approved
0.7113	Intermediate Similarity	NPD6776	Approved
0.7113	Intermediate Similarity	NPD6779	Approved
0.7108	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8455	Phase 2
0.7102	Intermediate Similarity	NPD5761	Phase 2
0.7102	Intermediate Similarity	NPD5760	Phase 2
0.71	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7783	Phase 2
0.7089	Intermediate Similarity	NPD1608	Approved
0.7085	Intermediate Similarity	NPD8151	Discontinued
0.7065	Intermediate Similarity	NPD1729	Discontinued
0.7063	Intermediate Similarity	NPD1164	Approved
0.7059	Intermediate Similarity	NPD3887	Approved
0.7055	Intermediate Similarity	NPD1296	Phase 2
0.7055	Intermediate Similarity	NPD411	Approved
0.7041	Intermediate Similarity	NPD1652	Phase 2
0.7037	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7585	Approved
0.7029	Intermediate Similarity	NPD6585	Discontinued
0.6994	Remote Similarity	NPD4625	Phase 3
0.6994	Remote Similarity	NPD7095	Approved
0.6989	Remote Similarity	NPD6765	Approved
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6989	Remote Similarity	NPD6764	Approved
0.6985	Remote Similarity	NPD7583	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