NPASS Compound

Structure

NPC474302 OpenBabel07101718252D 21 23 0 0 1 0 0 0 0 0999 V2000 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 19 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 6 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.12
Volume:	290.392
LogP:	2.794
LogD:	1.622
LogS:	-3.284
# Rotatable Bonds:	1
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.872
Synthetic Accessibility Score:	3.428
Fsp3:	0.438
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:	-4.785
MDCK Permeability:	1.3599352314486168e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.641
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	80.45113372802734%
Volume Distribution (VD):	1.049
Pgp-substrate:	17.132606506347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.703
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.624
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.696

ADMET: Excretion

Clearance (CL):	5.511
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.302
Carcinogencity:	0.49
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC474302

Natural Product ID:	NPC474302
*Common Name:**	(+)-5-Methoxyhamaudol
IUPAC Name:	(3R)-3-hydroxy-5-methoxy-2,2,8-trimethyl-3,4-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	(+)-5-Methoxyhamaudol
Standard InCHIKey:	SGCZPPRRLCNDAZ-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C16H18O5/c1-8-5-10(17)14-12(20-8)7-11-9(15(14)19-4)6-13(18)16(2,3)21-11/h5,7,13,18H,6H2,1-4H3/t13-/m1/s1
SMILES:	CC1=CC(=O)C2=C(C3=C(C=C2O1)OC(C(C3)O)(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464886
PubChem CID:	11033588
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
NPO32915	prionosciadium watsoni	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088423]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	383000.0	nM	PMID[448136]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	461000.0	nM	PMID[448136]

☑ 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 NPC474302 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	375
0.1-0.2	1555
0.2-0.3	3864
0.3-0.4	9458
0.4-0.5	9303
0.5-0.6	4028
0.6-0.7	5838
0.7-0.8	4525
0.8-0.85	2455
0.85-0.9	1145
0.9-0.95	145
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC85773
0.9718	High Similarity	NPC10097
0.965	High Similarity	NPC139966
0.965	High Similarity	NPC307052
0.9648	High Similarity	NPC473133
0.9648	High Similarity	NPC470670
0.9648	High Similarity	NPC91902
0.9648	High Similarity	NPC47388
0.9586	High Similarity	NPC256141
0.9521	High Similarity	NPC7989
0.9521	High Similarity	NPC469405
0.9521	High Similarity	NPC223701
0.9521	High Similarity	NPC472583
0.9517	High Similarity	NPC472422
0.9517	High Similarity	NPC474023
0.9517	High Similarity	NPC472420
0.9517	High Similarity	NPC263384
0.9517	High Similarity	NPC244577
0.9517	High Similarity	NPC471677
0.9517	High Similarity	NPC471676
0.9517	High Similarity	NPC474021
0.951	High Similarity	NPC202494
0.9456	High Similarity	NPC48579
0.9456	High Similarity	NPC259710
0.9456	High Similarity	NPC304207
0.9456	High Similarity	NPC217706
0.9456	High Similarity	NPC477530
0.9456	High Similarity	NPC207809
0.9452	High Similarity	NPC56232
0.9452	High Similarity	NPC475790
0.9452	High Similarity	NPC150123
0.9452	High Similarity	NPC161881
0.9452	High Similarity	NPC10807
0.9452	High Similarity	NPC244583
0.9448	High Similarity	NPC180351
0.9437	High Similarity	NPC18886
0.9392	High Similarity	NPC17521
0.9388	High Similarity	NPC248793
0.9388	High Similarity	NPC180301
0.9388	High Similarity	NPC88983
0.9384	High Similarity	NPC328740
0.9384	High Similarity	NPC289774
0.9384	High Similarity	NPC477897
0.9384	High Similarity	NPC262039
0.9384	High Similarity	NPC209846
0.9384	High Similarity	NPC471675
0.9384	High Similarity	NPC254412
0.9384	High Similarity	NPC262038
0.9384	High Similarity	NPC319910
0.9384	High Similarity	NPC472636
0.9384	High Similarity	NPC278476
0.9379	High Similarity	NPC472628
0.9375	High Similarity	NPC472627
0.9371	High Similarity	NPC224714
0.9371	High Similarity	NPC297788
0.9371	High Similarity	NPC87486
0.9371	High Similarity	NPC171656
0.9371	High Similarity	NPC124780
0.9371	High Similarity	NPC294365
0.9371	High Similarity	NPC470890
0.9324	High Similarity	NPC111341
0.9324	High Similarity	NPC470603
0.9324	High Similarity	NPC477958
0.9324	High Similarity	NPC470605
0.9324	High Similarity	NPC470604
0.9324	High Similarity	NPC470681
0.9324	High Similarity	NPC304745
0.932	High Similarity	NPC35567
0.932	High Similarity	NPC31627
0.932	High Similarity	NPC171651
0.932	High Similarity	NPC138288
0.932	High Similarity	NPC473996
0.932	High Similarity	NPC476238
0.932	High Similarity	NPC285623
0.932	High Similarity	NPC243171
0.932	High Similarity	NPC217149
0.932	High Similarity	NPC327269
0.932	High Similarity	NPC216035
0.9315	High Similarity	NPC105136
0.9306	High Similarity	NPC472629
0.9301	High Similarity	NPC242100
0.9301	High Similarity	NPC255133
0.9291	High Similarity	NPC471697
0.9291	High Similarity	NPC139554
0.9267	High Similarity	NPC470607
0.9262	High Similarity	NPC20530
0.9262	High Similarity	NPC215917
0.9262	High Similarity	NPC10754
0.9257	High Similarity	NPC311579
0.9257	High Similarity	NPC211158
0.9257	High Similarity	NPC268193
0.9257	High Similarity	NPC326592
0.9257	High Similarity	NPC108706
0.9257	High Similarity	NPC268950
0.9257	High Similarity	NPC112701
0.9257	High Similarity	NPC87304
0.9257	High Similarity	NPC78021
0.9257	High Similarity	NPC293286
0.9257	High Similarity	NPC236756
0.9257	High Similarity	NPC109594
0.9252	High Similarity	NPC472423
0.9252	High Similarity	NPC474772
0.9252	High Similarity	NPC474744
0.9252	High Similarity	NPC472580
0.9247	High Similarity	NPC5173
0.9247	High Similarity	NPC89442
0.9241	High Similarity	NPC296998
0.9241	High Similarity	NPC222298
0.9241	High Similarity	NPC51070
0.9241	High Similarity	NPC473077
0.9231	High Similarity	NPC276565
0.922	High Similarity	NPC131130
0.9205	High Similarity	NPC475784
0.92	High Similarity	NPC470606
0.9195	High Similarity	NPC476169
0.9189	High Similarity	NPC210597
0.9189	High Similarity	NPC477957
0.9184	High Similarity	NPC61258
0.9184	High Similarity	NPC177308
0.9184	High Similarity	NPC472633
0.9184	High Similarity	NPC472421
0.9184	High Similarity	NPC124478
0.9172	High Similarity	NPC54577
0.9172	High Similarity	NPC88964
0.9172	High Similarity	NPC142405
0.9172	High Similarity	NPC67805
0.9172	High Similarity	NPC176229
0.9172	High Similarity	NPC470647
0.9172	High Similarity	NPC267375
0.9172	High Similarity	NPC20488
0.9172	High Similarity	NPC195621
0.9172	High Similarity	NPC316769
0.9172	High Similarity	NPC246948
0.9172	High Similarity	NPC301276
0.9172	High Similarity	NPC111786
0.9172	High Similarity	NPC290133
0.9172	High Similarity	NPC187282
0.9172	High Similarity	NPC214774
0.9172	High Similarity	NPC475052
0.9172	High Similarity	NPC24136
0.9172	High Similarity	NPC83357
0.9172	High Similarity	NPC312973
0.9167	High Similarity	NPC112749
0.9167	High Similarity	NPC214166
0.9167	High Similarity	NPC478086
0.9167	High Similarity	NPC316816
0.9161	High Similarity	NPC258630
0.9161	High Similarity	NPC156190
0.9161	High Similarity	NPC279650
0.9161	High Similarity	NPC96408
0.9161	High Similarity	NPC166689
0.9161	High Similarity	NPC17170
0.9161	High Similarity	NPC74397
0.9155	High Similarity	NPC23257
0.9145	High Similarity	NPC474038
0.9139	High Similarity	NPC473990
0.9133	High Similarity	NPC208152
0.9133	High Similarity	NPC78492
0.9133	High Similarity	NPC164427
0.9128	High Similarity	NPC244250
0.9128	High Similarity	NPC74924
0.9128	High Similarity	NPC209760
0.9128	High Similarity	NPC100134
0.9128	High Similarity	NPC20907
0.9116	High Similarity	NPC164299
0.911	High Similarity	NPC23728
0.911	High Similarity	NPC44721
0.911	High Similarity	NPC211466
0.911	High Similarity	NPC476182
0.911	High Similarity	NPC40086
0.911	High Similarity	NPC122828
0.911	High Similarity	NPC176869
0.911	High Similarity	NPC283234
0.911	High Similarity	NPC110303
0.911	High Similarity	NPC472918
0.911	High Similarity	NPC3779
0.9103	High Similarity	NPC209040
0.9103	High Similarity	NPC131568
0.9103	High Similarity	NPC131579
0.9097	High Similarity	NPC64915
0.9097	High Similarity	NPC148757
0.9097	High Similarity	NPC306829
0.9097	High Similarity	NPC40833
0.9097	High Similarity	NPC166934
0.9097	High Similarity	NPC1089
0.9097	High Similarity	NPC125855
0.9097	High Similarity	NPC167624
0.9097	High Similarity	NPC107572
0.9097	High Similarity	NPC324436
0.9097	High Similarity	NPC227579
0.9097	High Similarity	NPC324134
0.9097	High Similarity	NPC76372
0.9097	High Similarity	NPC161506
0.9097	High Similarity	NPC32739
0.9097	High Similarity	NPC147145
0.9097	High Similarity	NPC37496
0.9097	High Similarity	NPC78
0.9097	High Similarity	NPC166482
0.9097	High Similarity	NPC194432
0.9097	High Similarity	NPC223500

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 NPC474302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	891
0.2-0.3	1761
0.3-0.4	2689
0.4-0.5	1864
0.5-0.6	1078
0.6-0.7	361
0.7-0.8	122
0.8-0.85	39
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9184	High Similarity	NPD4380	Phase 2
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD7096	Clinical (unspecified phase)
0.8973	High Similarity	NPD4378	Clinical (unspecified phase)
0.8824	High Similarity	NPD7075	Discontinued
0.8824	High Similarity	NPD4381	Clinical (unspecified phase)
0.8811	High Similarity	NPD2796	Approved
0.8808	High Similarity	NPD1934	Approved
0.8808	High Similarity	NPD6801	Discontinued
0.875	High Similarity	NPD1552	Clinical (unspecified phase)
0.875	High Similarity	NPD1550	Clinical (unspecified phase)
0.869	High Similarity	NPD1549	Phase 2
0.8679	High Similarity	NPD7804	Clinical (unspecified phase)
0.8591	High Similarity	NPD7410	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8523	High Similarity	NPD6799	Approved
0.8506	High Similarity	NPD7819	Suspended
0.8506	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD7411	Suspended
0.8491	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6166	Phase 2
0.8483	Intermediate Similarity	NPD1510	Phase 2
0.8452	Intermediate Similarity	NPD3817	Phase 2
0.84	Intermediate Similarity	NPD1511	Approved
0.8354	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD7054	Approved
0.8312	Intermediate Similarity	NPD6599	Discontinued
0.8302	Intermediate Similarity	NPD6959	Discontinued
0.8289	Intermediate Similarity	NPD1512	Approved
0.8282	Intermediate Similarity	NPD7472	Approved
0.8282	Intermediate Similarity	NPD7074	Phase 3
0.8272	Intermediate Similarity	NPD3818	Discontinued
0.8255	Intermediate Similarity	NPD2800	Approved
0.8235	Intermediate Similarity	NPD5403	Approved
0.8232	Intermediate Similarity	NPD6797	Phase 2
0.8224	Intermediate Similarity	NPD5401	Approved
0.8207	Intermediate Similarity	NPD1240	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8165	Intermediate Similarity	NPD3882	Suspended
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1243	Approved
0.8133	Intermediate Similarity	NPD7808	Phase 3
0.8117	Intermediate Similarity	NPD920	Approved
0.8101	Intermediate Similarity	NPD5402	Approved
0.8095	Intermediate Similarity	NPD1607	Approved
0.8067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6651	Approved
0.7961	Intermediate Similarity	NPD4628	Phase 3
0.7947	Intermediate Similarity	NPD2424	Discontinued
0.7945	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7905	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5124	Phase 1
0.7853	Intermediate Similarity	NPD1247	Approved
0.7843	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3750	Approved
0.784	Intermediate Similarity	NPD919	Approved
0.7823	Intermediate Similarity	NPD2313	Discontinued
0.7811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6232	Discontinued
0.7798	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1652	Phase 2
0.7778	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7748	Intermediate Similarity	NPD3748	Approved
0.7748	Intermediate Similarity	NPD7033	Discontinued
0.7748	Intermediate Similarity	NPD2799	Discontinued
0.7697	Intermediate Similarity	NPD6099	Approved
0.7697	Intermediate Similarity	NPD2935	Discontinued
0.7697	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD6100	Approved
0.7692	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4363	Phase 3
0.767	Intermediate Similarity	NPD4360	Phase 2
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1613	Approved
0.7596	Intermediate Similarity	NPD7584	Approved
0.759	Intermediate Similarity	NPD3787	Discontinued
0.7588	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7286	Phase 2
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD2403	Approved
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7469	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6798	Discontinued
0.7453	Intermediate Similarity	NPD3226	Approved
0.745	Intermediate Similarity	NPD6832	Phase 2
0.745	Intermediate Similarity	NPD4908	Phase 1
0.744	Intermediate Similarity	NPD3926	Phase 2
0.7434	Intermediate Similarity	NPD230	Phase 1
0.7432	Intermediate Similarity	NPD2798	Approved
0.7419	Intermediate Similarity	NPD2344	Approved
0.7403	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD9717	Approved
0.7384	Intermediate Similarity	NPD3823	Discontinued
0.7383	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD943	Approved
0.7358	Intermediate Similarity	NPD7390	Discontinued
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7351	Intermediate Similarity	NPD3268	Approved
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4361	Phase 2
0.733	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1610	Phase 2
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD447	Suspended
0.732	Intermediate Similarity	NPD1933	Approved
0.7317	Intermediate Similarity	NPD6844	Discontinued
0.7312	Intermediate Similarity	NPD4661	Approved
0.7312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4662	Approved
0.7303	Intermediate Similarity	NPD6233	Phase 2
0.7297	Intermediate Similarity	NPD8651	Approved
0.7292	Intermediate Similarity	NPD1548	Phase 1
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD3027	Phase 3
0.7284	Intermediate Similarity	NPD1653	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7248	Intermediate Similarity	NPD1203	Approved
0.7248	Intermediate Similarity	NPD2797	Approved
0.7241	Intermediate Similarity	NPD6104	Discontinued
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7233	Intermediate Similarity	NPD2309	Approved
0.723	Intermediate Similarity	NPD4749	Approved
0.7226	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD4536	Approved
0.7226	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7583	Approved
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD37	Approved
0.7211	Intermediate Similarity	NPD1091	Approved
0.7208	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1019	Discontinued
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7193	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4966	Approved
0.7186	Intermediate Similarity	NPD4967	Phase 2
0.7186	Intermediate Similarity	NPD4965	Approved
0.7183	Intermediate Similarity	NPD1241	Discontinued
0.7181	Intermediate Similarity	NPD7585	Approved
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.7174	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4625	Phase 3
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD5889	Approved
0.7152	Intermediate Similarity	NPD5890	Approved
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7126	Intermediate Similarity	NPD2415	Discontinued
0.7126	Intermediate Similarity	NPD1729	Discontinued
0.7126	Intermediate Similarity	NPD5353	Approved
0.7125	Intermediate Similarity	NPD2354	Approved
0.7125	Intermediate Similarity	NPD3887	Approved
0.7115	Intermediate Similarity	NPD7097	Phase 1

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