NPASS Compound

Structure

CID180351 OpenBabel06191715552D 26 28 0 0 1 0 0 0 0 0999 V2000 -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 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 -3.4641 3.0000 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 -3.4641 2.0000 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 1 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -1.7321 2.0000 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 26 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 1 0 0 0 17 18 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	363.093
LogP:	4.204
LogD:	2.808
LogS:	-3.146
# Rotatable Bonds:	3
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.654
Synthetic Accessibility Score:	3.659
Fsp3:	0.4
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:	-4.683
MDCK Permeability:	2.1333493350539356e-05
Pgp-inhibitor:	0.831
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.574

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	83.86304473876953%
Volume Distribution (VD):	0.823
Pgp-substrate:	10.684188842773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.64
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.443
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.486
CYP2D6-substrate:	0.404
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	3.927
Half-life (T1/2):	0.325

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.332
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.558
Carcinogencity:	0.699
Eye Corrosion:	0.004
Eye Irritation:	0.116
Respiratory Toxicity:	0.575

Download Data

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

Natural Product: NPC180351

Natural Product ID:	NPC180351
*Common Name:**	3-O-Angeloylhamaudol
IUPAC Name:	[(3S)-5-hydroxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate
Synonyms:	3-O-Angeloylhamaudol
Standard InCHIKey:	GLVOOJKVWKZSGR-DIEDAUMRSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-6-10(2)19(23)25-16-8-12-14(26-20(16,4)5)9-15-17(18(12)22)13(21)7-11(3)24-15/h6-7,9,16,22H,8H2,1-5H3/b10-6-/t16-/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@H]1Cc2c(cc3c(c(=O)cc(C)o3)c2O)OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2059289
PubChem CID:	56643444
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
NPO24768	Sphallerocarpus gracilis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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[495431]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	97.8	%	PMID[495431]

☑ 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 NPC180351 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	354
0.1-0.2	1499
0.2-0.3	3738
0.3-0.4	8299
0.4-0.5	10310
0.5-0.6	3810
0.6-0.7	5725
0.7-0.8	4454
0.8-0.85	2891
0.85-0.9	1391
0.9-0.95	220
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC256141
0.965	High Similarity	NPC171656
0.9517	High Similarity	NPC85773
0.9514	High Similarity	NPC294365
0.9452	High Similarity	NPC10097
0.9448	High Similarity	NPC474302
0.9396	High Similarity	NPC223701
0.9396	High Similarity	NPC472583
0.9396	High Similarity	NPC7989
0.9396	High Similarity	NPC469405
0.9392	High Similarity	NPC244577
0.9392	High Similarity	NPC472420
0.9392	High Similarity	NPC472422
0.9392	High Similarity	NPC471676
0.9392	High Similarity	NPC263384
0.9388	High Similarity	NPC307052
0.9388	High Similarity	NPC139966
0.9384	High Similarity	NPC473133
0.9384	High Similarity	NPC47388
0.9384	High Similarity	NPC470670
0.9384	High Similarity	NPC91902
0.9333	High Similarity	NPC279218
0.9333	High Similarity	NPC108937
0.9329	High Similarity	NPC476238
0.9329	High Similarity	NPC31627
0.9329	High Similarity	NPC327269
0.9329	High Similarity	NPC473996
0.9272	High Similarity	NPC475797
0.9272	High Similarity	NPC129053
0.9272	High Similarity	NPC474609
0.9272	High Similarity	NPC78554
0.9272	High Similarity	NPC109967
0.9272	High Similarity	NPC321372
0.9272	High Similarity	NPC474738
0.9272	High Similarity	NPC469936
0.9267	High Similarity	NPC311579
0.9267	High Similarity	NPC236756
0.9262	High Similarity	NPC472636
0.9262	High Similarity	NPC472580
0.9262	High Similarity	NPC471677
0.9262	High Similarity	NPC474021
0.9262	High Similarity	NPC474023
0.9262	High Similarity	NPC471675
0.9257	High Similarity	NPC104236
0.9257	High Similarity	NPC164205
0.9257	High Similarity	NPC164299
0.9252	High Similarity	NPC285748
0.9252	High Similarity	NPC473077
0.9252	High Similarity	NPC296998
0.9252	High Similarity	NPC110303
0.9252	High Similarity	NPC23728
0.9252	High Similarity	NPC202494
0.9247	High Similarity	NPC316535
0.9247	High Similarity	NPC470890
0.9247	High Similarity	NPC469953
0.9247	High Similarity	NPC224714
0.9247	High Similarity	NPC209040
0.9241	High Similarity	NPC112829
0.9241	High Similarity	NPC294432
0.9241	High Similarity	NPC470556
0.9241	High Similarity	NPC276565
0.9231	High Similarity	NPC131130
0.9205	High Similarity	NPC470605
0.9205	High Similarity	NPC477958
0.9205	High Similarity	NPC470681
0.9205	High Similarity	NPC304207
0.9205	High Similarity	NPC48579
0.9205	High Similarity	NPC207809
0.9205	High Similarity	NPC217706
0.9205	High Similarity	NPC470604
0.9205	High Similarity	NPC259710
0.9205	High Similarity	NPC470603
0.92	High Similarity	NPC477957
0.92	High Similarity	NPC285623
0.92	High Similarity	NPC56232
0.92	High Similarity	NPC35567
0.92	High Similarity	NPC244583
0.92	High Similarity	NPC161881
0.92	High Similarity	NPC171651
0.92	High Similarity	NPC150123
0.92	High Similarity	NPC243171
0.92	High Similarity	NPC10807
0.92	High Similarity	NPC475790
0.9195	High Similarity	NPC472633
0.9195	High Similarity	NPC472421
0.9195	High Similarity	NPC321387
0.9195	High Similarity	NPC327059
0.9195	High Similarity	NPC474735
0.9195	High Similarity	NPC470908
0.9195	High Similarity	NPC61258
0.9189	High Similarity	NPC168085
0.9189	High Similarity	NPC132592
0.9189	High Similarity	NPC472345
0.9189	High Similarity	NPC211811
0.9189	High Similarity	NPC160821
0.9184	High Similarity	NPC24136
0.9184	High Similarity	NPC88964
0.9184	High Similarity	NPC54577
0.9184	High Similarity	NPC187282
0.9184	High Similarity	NPC111786
0.9184	High Similarity	NPC301276
0.9184	High Similarity	NPC290133
0.9184	High Similarity	NPC312973
0.9184	High Similarity	NPC195621
0.9184	High Similarity	NPC267375
0.9184	High Similarity	NPC475052
0.9184	High Similarity	NPC83357
0.9184	High Similarity	NPC470647
0.9184	High Similarity	NPC472629
0.9184	High Similarity	NPC20488
0.9184	High Similarity	NPC67805
0.9184	High Similarity	NPC176229
0.9184	High Similarity	NPC142405
0.9184	High Similarity	NPC246948
0.9184	High Similarity	NPC214774
0.9178	High Similarity	NPC307895
0.9178	High Similarity	NPC149026
0.9178	High Similarity	NPC175504
0.9178	High Similarity	NPC143896
0.9178	High Similarity	NPC470909
0.9178	High Similarity	NPC316816
0.9178	High Similarity	NPC150408
0.9178	High Similarity	NPC96216
0.9178	High Similarity	NPC33653
0.9178	High Similarity	NPC470553
0.9178	High Similarity	NPC91560
0.9178	High Similarity	NPC68104
0.9178	High Similarity	NPC75049
0.9178	High Similarity	NPC39329
0.9178	High Similarity	NPC257097
0.9178	High Similarity	NPC221432
0.9178	High Similarity	NPC18886
0.9178	High Similarity	NPC166138
0.9178	High Similarity	NPC18585
0.9178	High Similarity	NPC214166
0.9178	High Similarity	NPC169591
0.9178	High Similarity	NPC310130
0.9178	High Similarity	NPC474939
0.9178	High Similarity	NPC164980
0.9178	High Similarity	NPC478086
0.9178	High Similarity	NPC184738
0.9178	High Similarity	NPC106985
0.9172	High Similarity	NPC17170
0.9172	High Similarity	NPC166689
0.9172	High Similarity	NPC96408
0.9172	High Similarity	NPC258630
0.9172	High Similarity	NPC171870
0.9172	High Similarity	NPC156190
0.9172	High Similarity	NPC279650
0.9167	High Similarity	NPC139554
0.9167	High Similarity	NPC23257
0.9156	High Similarity	NPC92589
0.9156	High Similarity	NPC97812
0.915	High Similarity	NPC470607
0.9145	High Similarity	NPC471787
0.9139	High Similarity	NPC180301
0.9139	High Similarity	NPC268950
0.9139	High Similarity	NPC211158
0.9139	High Similarity	NPC108706
0.9139	High Similarity	NPC78021
0.9139	High Similarity	NPC248793
0.9139	High Similarity	NPC87304
0.9139	High Similarity	NPC293286
0.9133	High Similarity	NPC328740
0.9133	High Similarity	NPC254412
0.9133	High Similarity	NPC289774
0.9133	High Similarity	NPC472423
0.9133	High Similarity	NPC474772
0.9133	High Similarity	NPC477897
0.9133	High Similarity	NPC295650
0.9133	High Similarity	NPC209846
0.9133	High Similarity	NPC262039
0.9133	High Similarity	NPC319910
0.9133	High Similarity	NPC262038
0.9133	High Similarity	NPC290671
0.9133	High Similarity	NPC278476
0.9133	High Similarity	NPC474744
0.9128	High Similarity	NPC5173
0.9128	High Similarity	NPC472628
0.9128	High Similarity	NPC317492
0.9128	High Similarity	NPC477941
0.9128	High Similarity	NPC19238
0.9128	High Similarity	NPC89442
0.9122	High Similarity	NPC104406
0.9122	High Similarity	NPC24673
0.9122	High Similarity	NPC201731
0.9122	High Similarity	NPC472627
0.9122	High Similarity	NPC79469
0.9122	High Similarity	NPC283234
0.9122	High Similarity	NPC222298
0.9122	High Similarity	NPC97716
0.9122	High Similarity	NPC140120
0.9122	High Similarity	NPC177995
0.9122	High Similarity	NPC474108
0.9122	High Similarity	NPC51070
0.9122	High Similarity	NPC237635
0.9116	High Similarity	NPC473013
0.9116	High Similarity	NPC131568
0.9116	High Similarity	NPC87486
0.9116	High Similarity	NPC131579

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 NPC180351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	901
0.2-0.3	1771
0.3-0.4	2519
0.4-0.5	1968
0.5-0.6	1105
0.6-0.7	374
0.7-0.8	136
0.8-0.85	52
0.85-0.9	16
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD7075	Discontinued
0.9139	High Similarity	NPD7096	Clinical (unspecified phase)
0.9067	High Similarity	NPD4380	Phase 2
0.8986	High Similarity	NPD4378	Clinical (unspecified phase)
0.8947	High Similarity	NPD6801	Discontinued
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8882	High Similarity	NPD7411	Suspended
0.8839	High Similarity	NPD4381	Clinical (unspecified phase)
0.8836	High Similarity	NPD1549	Phase 2
0.8767	High Similarity	NPD1552	Clinical (unspecified phase)
0.8767	High Similarity	NPD1550	Clinical (unspecified phase)
0.8766	High Similarity	NPD7819	Suspended
0.8733	High Similarity	NPD7410	Clinical (unspecified phase)
0.8701	High Similarity	NPD1934	Approved
0.8699	High Similarity	NPD2796	Approved
0.8667	High Similarity	NPD6799	Approved
0.863	High Similarity	NPD1510	Phase 2
0.859	High Similarity	NPD8443	Clinical (unspecified phase)
0.858	High Similarity	NPD7804	Clinical (unspecified phase)
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8509	High Similarity	NPD7852	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD3817	Phase 2
0.8456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6599	Discontinued
0.8418	Intermediate Similarity	NPD7768	Phase 2
0.8408	Intermediate Similarity	NPD2801	Approved
0.84	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1243	Approved
0.8377	Intermediate Similarity	NPD920	Approved
0.8377	Intermediate Similarity	NPD5403	Approved
0.8366	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD2532	Approved
0.8366	Intermediate Similarity	NPD2534	Approved
0.8356	Intermediate Similarity	NPD1240	Approved
0.8344	Intermediate Similarity	NPD3750	Approved
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8313	Intermediate Similarity	NPD6559	Discontinued
0.8301	Intermediate Similarity	NPD1511	Approved
0.8293	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6166	Phase 2
0.8282	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2800	Approved
0.8261	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD3749	Approved
0.8247	Intermediate Similarity	NPD5401	Approved
0.8247	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1607	Approved
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8242	Intermediate Similarity	NPD7054	Approved
0.8239	Intermediate Similarity	NPD5402	Approved
0.8235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2935	Discontinued
0.82	Intermediate Similarity	NPD1551	Phase 2
0.8194	Intermediate Similarity	NPD1512	Approved
0.8193	Intermediate Similarity	NPD7472	Approved
0.8193	Intermediate Similarity	NPD7074	Phase 3
0.8187	Intermediate Similarity	NPD3882	Suspended
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8155	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6797	Phase 2
0.8121	Intermediate Similarity	NPD7473	Discontinued
0.8105	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD4628	Phase 3
0.8095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2313	Discontinued
0.8095	Intermediate Similarity	NPD7251	Discontinued
0.8086	Intermediate Similarity	NPD919	Approved
0.8054	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD5124	Phase 1
0.8047	Intermediate Similarity	NPD7808	Phase 3
0.8036	Intermediate Similarity	NPD5953	Discontinued
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7286	Phase 2
0.8013	Intermediate Similarity	NPD2799	Discontinued
0.8013	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD6651	Approved
0.7895	Intermediate Similarity	NPD7033	Discontinued
0.784	Intermediate Similarity	NPD1465	Phase 2
0.7831	Intermediate Similarity	NPD5710	Approved
0.7831	Intermediate Similarity	NPD5711	Approved
0.7815	Intermediate Similarity	NPD230	Phase 1
0.7812	Intermediate Similarity	NPD3226	Approved
0.7809	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD9717	Approved
0.7792	Intermediate Similarity	NPD2346	Discontinued
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1247	Approved
0.7755	Intermediate Similarity	NPD1203	Approved
0.7733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7724	Intermediate Similarity	NPD422	Phase 1
0.7718	Intermediate Similarity	NPD6832	Phase 2
0.7716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD1652	Phase 2
0.7662	Intermediate Similarity	NPD4308	Phase 3
0.7622	Intermediate Similarity	NPD7584	Approved
0.7616	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3268	Approved
0.7603	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD4363	Phase 3
0.7598	Intermediate Similarity	NPD4360	Phase 2
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7586	Intermediate Similarity	NPD8312	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.7578	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD9545	Approved
0.7564	Intermediate Similarity	NPD2344	Approved
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1653	Approved
0.7517	Intermediate Similarity	NPD2797	Approved
0.7516	Intermediate Similarity	NPD2424	Discontinued
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2798	Approved
0.7467	Intermediate Similarity	NPD1019	Discontinued
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3751	Discontinued
0.7431	Intermediate Similarity	NPD9493	Approved
0.7427	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1613	Approved
0.7403	Intermediate Similarity	NPD4307	Phase 2
0.7394	Intermediate Similarity	NPD7585	Approved
0.7394	Intermediate Similarity	NPD5890	Approved
0.7394	Intermediate Similarity	NPD5889	Approved
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7386	Intermediate Similarity	NPD1296	Phase 2
0.7386	Intermediate Similarity	NPD411	Approved
0.7375	Intermediate Similarity	NPD3887	Approved
0.7375	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3926	Phase 2
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7365	Intermediate Similarity	NPD5353	Approved
0.7365	Intermediate Similarity	NPD4288	Approved
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.736	Intermediate Similarity	NPD8150	Discontinued
0.7358	Intermediate Similarity	NPD2654	Approved
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7354	Intermediate Similarity	NPD8151	Discontinued
0.7349	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6002	Phase 3
0.7342	Intermediate Similarity	NPD6005	Phase 3
0.7342	Intermediate Similarity	NPD6004	Phase 3
0.7342	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7583	Approved
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD3225	Approved
0.7333	Intermediate Similarity	NPD6585	Discontinued
0.7329	Intermediate Similarity	NPD1548	Phase 1
0.7326	Intermediate Similarity	NPD2403	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD3787	Discontinued
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5049	Phase 3
0.7297	Intermediate Similarity	NPD6776	Approved
0.7297	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6777	Approved
0.7297	Intermediate Similarity	NPD6782	Approved
0.7297	Intermediate Similarity	NPD6778	Approved
0.7297	Intermediate Similarity	NPD6779	Approved
0.7297	Intermediate Similarity	NPD6780	Approved
0.7285	Intermediate Similarity	NPD3266	Approved
0.7285	Intermediate Similarity	NPD3267	Approved
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3764	Approved
0.7268	Intermediate Similarity	NPD4361	Phase 2
0.7268	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4749	Approved
0.7267	Intermediate Similarity	NPD2354	Approved
0.7267	Intermediate Similarity	NPD6190	Approved
0.7261	Intermediate Similarity	NPD7097	Phase 1
0.7257	Intermediate Similarity	NPD1729	Discontinued
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3823	Discontinued
0.7208	Intermediate Similarity	NPD4625	Phase 3
0.7205	Intermediate Similarity	NPD7003	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