NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	2.803
LogD:	1.759
LogS:	-2.903
# Rotatable Bonds:	0
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	3.433
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	1.2485994375310838e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.821
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.839

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	83.51700592041016%
Volume Distribution (VD):	0.759
Pgp-substrate:	15.63862419128418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.765
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.559
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.351
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	7.034
Half-life (T1/2):	0.419

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.594
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC85773

Natural Product ID:	NPC85773
*Common Name:**	Hamaudol
IUPAC Name:	(3S)-3,5-dihydroxy-2,2,8-trimethyl-3,4-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	Hamaudol
Standard InCHIKey:	VOTLUFSYIRHICX-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-7-4-9(16)13-11(19-7)6-10-8(14(13)18)5-12(17)15(2,3)20-10/h4,6,12,17-18H,5H2,1-3H3/t12-/m0/s1
SMILES:	Cc1cc(=O)c2c(o1)cc1c(c2O)C[C@@H](C(O1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2059288
PubChem CID:	164722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1453177]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17703773]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16675	Peucedanum japonicum	Species	Apiaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	104.8	%	PMID[518236]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	98.2	%	PMID[518236]

☑ 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 NPC85773 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	379
0.1-0.2	1590
0.2-0.3	3993
0.3-0.4	9534
0.4-0.5	8999
0.5-0.6	3878
0.6-0.7	5599
0.7-0.8	4544
0.8-0.85	2370
0.85-0.9	1574
0.9-0.95	223
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC10097
0.9787	High Similarity	NPC474302
0.972	High Similarity	NPC307052
0.972	High Similarity	NPC139966
0.9718	High Similarity	NPC470670
0.9718	High Similarity	NPC202494
0.9718	High Similarity	NPC47388
0.9718	High Similarity	NPC473133
0.9718	High Similarity	NPC91902
0.9655	High Similarity	NPC256141
0.9589	High Similarity	NPC7989
0.9589	High Similarity	NPC223701
0.9589	High Similarity	NPC469405
0.9589	High Similarity	NPC472583
0.9586	High Similarity	NPC474021
0.9586	High Similarity	NPC472422
0.9586	High Similarity	NPC471677
0.9586	High Similarity	NPC471676
0.9586	High Similarity	NPC474023
0.9586	High Similarity	NPC244577
0.9586	High Similarity	NPC472420
0.9586	High Similarity	NPC263384
0.9577	High Similarity	NPC297788
0.9524	High Similarity	NPC304207
0.9524	High Similarity	NPC207809
0.9524	High Similarity	NPC48579
0.9524	High Similarity	NPC217706
0.9524	High Similarity	NPC259710
0.9521	High Similarity	NPC161881
0.9521	High Similarity	NPC150123
0.9521	High Similarity	NPC475790
0.9521	High Similarity	NPC10807
0.9521	High Similarity	NPC56232
0.9521	High Similarity	NPC244583
0.9517	High Similarity	NPC180351
0.9507	High Similarity	NPC255133
0.9507	High Similarity	NPC242100
0.9507	High Similarity	NPC18886
0.95	High Similarity	NPC471697
0.9456	High Similarity	NPC180301
0.9456	High Similarity	NPC248793
0.9452	High Similarity	NPC254412
0.9452	High Similarity	NPC209846
0.9452	High Similarity	NPC289774
0.9452	High Similarity	NPC471675
0.9452	High Similarity	NPC262038
0.9452	High Similarity	NPC328740
0.9452	High Similarity	NPC472636
0.9452	High Similarity	NPC262039
0.9452	High Similarity	NPC278476
0.9452	High Similarity	NPC319910
0.9452	High Similarity	NPC477897
0.9448	High Similarity	NPC472628
0.9444	High Similarity	NPC472627
0.9441	High Similarity	NPC470890
0.9441	High Similarity	NPC224714
0.9392	High Similarity	NPC470604
0.9392	High Similarity	NPC470681
0.9392	High Similarity	NPC304745
0.9392	High Similarity	NPC470603
0.9392	High Similarity	NPC111341
0.9392	High Similarity	NPC477958
0.9392	High Similarity	NPC470605
0.9388	High Similarity	NPC171651
0.9388	High Similarity	NPC473996
0.9388	High Similarity	NPC216035
0.9388	High Similarity	NPC217149
0.9388	High Similarity	NPC243171
0.9388	High Similarity	NPC31627
0.9388	High Similarity	NPC285623
0.9388	High Similarity	NPC35567
0.9388	High Similarity	NPC138288
0.9388	High Similarity	NPC327269
0.9388	High Similarity	NPC476238
0.9384	High Similarity	NPC105136
0.9375	High Similarity	NPC472629
0.9362	High Similarity	NPC139554
0.9333	High Similarity	NPC470607
0.9329	High Similarity	NPC10754
0.9329	High Similarity	NPC20530
0.9329	High Similarity	NPC215917
0.9324	High Similarity	NPC293286
0.9324	High Similarity	NPC268950
0.9324	High Similarity	NPC211158
0.9324	High Similarity	NPC108706
0.9324	High Similarity	NPC78021
0.9324	High Similarity	NPC109594
0.9324	High Similarity	NPC236756
0.9324	High Similarity	NPC87304
0.9324	High Similarity	NPC326592
0.9324	High Similarity	NPC112701
0.9324	High Similarity	NPC268193
0.9324	High Similarity	NPC311579
0.932	High Similarity	NPC472580
0.932	High Similarity	NPC472423
0.932	High Similarity	NPC474744
0.932	High Similarity	NPC474772
0.9315	High Similarity	NPC89442
0.9315	High Similarity	NPC5173
0.931	High Similarity	NPC296998
0.931	High Similarity	NPC222298
0.931	High Similarity	NPC473077
0.931	High Similarity	NPC51070
0.9306	High Similarity	NPC87486
0.9306	High Similarity	NPC124780
0.9301	High Similarity	NPC276565
0.9291	High Similarity	NPC131130
0.9272	High Similarity	NPC475784
0.9267	High Similarity	NPC470606
0.9262	High Similarity	NPC476169
0.9262	High Similarity	NPC477530
0.9257	High Similarity	NPC477957
0.9257	High Similarity	NPC210597
0.9252	High Similarity	NPC472421
0.9252	High Similarity	NPC61258
0.9252	High Similarity	NPC472633
0.9252	High Similarity	NPC124478
0.9252	High Similarity	NPC177308
0.9241	High Similarity	NPC301276
0.9241	High Similarity	NPC267375
0.9241	High Similarity	NPC214774
0.9241	High Similarity	NPC20488
0.9241	High Similarity	NPC312973
0.9241	High Similarity	NPC176229
0.9241	High Similarity	NPC290133
0.9241	High Similarity	NPC83357
0.9241	High Similarity	NPC24136
0.9241	High Similarity	NPC142405
0.9241	High Similarity	NPC246948
0.9241	High Similarity	NPC54577
0.9241	High Similarity	NPC67805
0.9241	High Similarity	NPC88964
0.9241	High Similarity	NPC470647
0.9241	High Similarity	NPC475052
0.9241	High Similarity	NPC316769
0.9241	High Similarity	NPC111786
0.9241	High Similarity	NPC187282
0.9241	High Similarity	NPC195621
0.9236	High Similarity	NPC112749
0.9236	High Similarity	NPC478086
0.9236	High Similarity	NPC214166
0.9236	High Similarity	NPC316816
0.9231	High Similarity	NPC17170
0.9231	High Similarity	NPC96408
0.9231	High Similarity	NPC74397
0.9231	High Similarity	NPC166689
0.9231	High Similarity	NPC279650
0.9231	High Similarity	NPC258630
0.9231	High Similarity	NPC171870
0.9231	High Similarity	NPC156190
0.9225	High Similarity	NPC23257
0.9214	High Similarity	NPC60667
0.9214	High Similarity	NPC84699
0.9211	High Similarity	NPC474038
0.9205	High Similarity	NPC473990
0.92	High Similarity	NPC208152
0.92	High Similarity	NPC17521
0.92	High Similarity	NPC164427
0.92	High Similarity	NPC78492
0.9195	High Similarity	NPC20907
0.9195	High Similarity	NPC244250
0.9195	High Similarity	NPC88983
0.9195	High Similarity	NPC100134
0.9195	High Similarity	NPC74924
0.9195	High Similarity	NPC209760
0.9178	High Similarity	NPC472918
0.9178	High Similarity	NPC122828
0.9178	High Similarity	NPC23728
0.9178	High Similarity	NPC211466
0.9178	High Similarity	NPC40086
0.9178	High Similarity	NPC3779
0.9178	High Similarity	NPC476182
0.9178	High Similarity	NPC283234
0.9178	High Similarity	NPC110303
0.9178	High Similarity	NPC21835
0.9178	High Similarity	NPC176869
0.9178	High Similarity	NPC44721
0.9172	High Similarity	NPC306607
0.9172	High Similarity	NPC131568
0.9172	High Similarity	NPC279417
0.9172	High Similarity	NPC294365
0.9172	High Similarity	NPC62290
0.9172	High Similarity	NPC131579
0.9172	High Similarity	NPC49130
0.9172	High Similarity	NPC326506
0.9172	High Similarity	NPC4152
0.9172	High Similarity	NPC142731
0.9172	High Similarity	NPC171656
0.9172	High Similarity	NPC208176
0.9172	High Similarity	NPC209040
0.9167	High Similarity	NPC220998
0.9167	High Similarity	NPC64915
0.9167	High Similarity	NPC32739
0.9167	High Similarity	NPC265040
0.9167	High Similarity	NPC328164
0.9167	High Similarity	NPC228504
0.9167	High Similarity	NPC296917
0.9167	High Similarity	NPC148757
0.9167	High Similarity	NPC227579
0.9167	High Similarity	NPC76372

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 NPC85773 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	894
0.2-0.3	1818
0.3-0.4	2652
0.4-0.5	1855
0.5-0.6	1048
0.6-0.7	368
0.7-0.8	123
0.8-0.85	37
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9252	High Similarity	NPD4380	Phase 2
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.9041	High Similarity	NPD4378	Clinical (unspecified phase)
0.8951	High Similarity	NPD1552	Clinical (unspecified phase)
0.8951	High Similarity	NPD1550	Clinical (unspecified phase)
0.8889	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD4381	Clinical (unspecified phase)
0.8889	High Similarity	NPD7075	Discontinued
0.8874	High Similarity	NPD1934	Approved
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.875	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD7804	Clinical (unspecified phase)
0.8681	High Similarity	NPD1510	Phase 2
0.8658	High Similarity	NPD7410	Clinical (unspecified phase)
0.8636	High Similarity	NPD8443	Clinical (unspecified phase)
0.8621	High Similarity	NPD2796	Approved
0.8591	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2801	Approved
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8477	Intermediate Similarity	NPD1512	Approved
0.8442	Intermediate Similarity	NPD7411	Suspended
0.8403	Intermediate Similarity	NPD1240	Approved
0.8395	Intermediate Similarity	NPD7054	Approved
0.8365	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD6799	Approved
0.8344	Intermediate Similarity	NPD7472	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8322	Intermediate Similarity	NPD2800	Approved
0.8293	Intermediate Similarity	NPD6797	Phase 2
0.8288	Intermediate Similarity	NPD1607	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8242	Intermediate Similarity	NPD7251	Discontinued
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8187	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD5403	Approved
0.8141	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1243	Approved
0.8065	Intermediate Similarity	NPD920	Approved
0.8052	Intermediate Similarity	NPD5401	Approved
0.8052	Intermediate Similarity	NPD2532	Approved
0.8052	Intermediate Similarity	NPD2534	Approved
0.8052	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD5402	Approved
0.8041	Intermediate Similarity	NPD6651	Approved
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3750	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.787	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5124	Phase 1
0.784	Intermediate Similarity	NPD3749	Approved
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7805	Intermediate Similarity	NPD1247	Approved
0.7791	Intermediate Similarity	NPD919	Approved
0.7785	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD2424	Discontinued
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6099	Approved
0.7763	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD4363	Phase 3
0.7727	Intermediate Similarity	NPD4360	Phase 2
0.7727	Intermediate Similarity	NPD1652	Phase 2
0.7697	Intermediate Similarity	NPD7033	Discontinued
0.7677	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.765	Intermediate Similarity	NPD7584	Approved
0.7647	Intermediate Similarity	NPD5953	Discontinued
0.764	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7286	Phase 2
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7582	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3748	Approved
0.7568	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD943	Approved
0.7545	Intermediate Similarity	NPD5710	Approved
0.7545	Intermediate Similarity	NPD5711	Approved
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7484	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7466	Intermediate Similarity	NPD9717	Approved
0.7453	Intermediate Similarity	NPD1653	Approved
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7432	Intermediate Similarity	NPD1203	Approved
0.7423	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7390	Discontinued
0.7417	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7407	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD2654	Approved
0.7389	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4361	Phase 2
0.7386	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7353	Intermediate Similarity	NPD2403	Approved
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7341	Intermediate Similarity	NPD3823	Discontinued
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7322	Intermediate Similarity	NPD6776	Approved
0.7322	Intermediate Similarity	NPD6779	Approved
0.7322	Intermediate Similarity	NPD6780	Approved
0.7322	Intermediate Similarity	NPD6777	Approved
0.7322	Intermediate Similarity	NPD6778	Approved
0.7322	Intermediate Similarity	NPD6781	Approved
0.7322	Intermediate Similarity	NPD6782	Approved
0.7303	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7296	Intermediate Similarity	NPD2309	Approved
0.7294	Intermediate Similarity	NPD3926	Phase 2
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7283	Intermediate Similarity	NPD1729	Discontinued
0.7279	Intermediate Similarity	NPD1091	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2798	Approved
0.7244	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4308	Phase 3
0.7241	Intermediate Similarity	NPD9545	Approved
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7234	Intermediate Similarity	NPD7585	Approved
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7435	Discontinued
0.72	Intermediate Similarity	NPD2797	Approved
0.7196	Intermediate Similarity	NPD8151	Discontinued
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8150	Discontinued
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7181	Intermediate Similarity	NPD7583	Approved
0.7178	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7169	Intermediate Similarity	NPD37	Approved
0.7169	Intermediate Similarity	NPD6844	Discontinued
0.7161	Intermediate Similarity	NPD1933	Approved
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD4662	Approved
0.716	Intermediate Similarity	NPD4661	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7133	Intermediate Similarity	NPD1241	Discontinued
0.7133	Intermediate Similarity	NPD8651	Approved
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7696	Phase 3
0.7112	Intermediate Similarity	NPD7698	Approved
0.7112	Intermediate Similarity	NPD7697	Approved
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9494	Approved
0.7103	Intermediate Similarity	NPD9493	Approved
0.7102	Intermediate Similarity	NPD6104	Discontinued
0.7081	Intermediate Similarity	NPD6190	Approved
0.7078	Intermediate Similarity	NPD411	Approved
0.7074	Intermediate Similarity	NPD7870	Phase 2
0.7074	Intermediate Similarity	NPD7871	Phase 2
0.707	Intermediate Similarity	NPD4538	Approved
0.707	Intermediate Similarity	NPD4536	Approved
0.707	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7228	Approved
0.7063	Intermediate Similarity	NPD5698	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