NPASS Compound

Structure

CID281137 OpenBabel06191716092D 37 40 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 0.8660 1.5000 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 8.6603 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 1.7321 2.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 16 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 30 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 28 2 0 0 0 0 20 29 1 0 0 0 0 21 31 1 6 0 0 0 22 32 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 29 2 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 34 2 0 0 0 0 26 27 2 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 36 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.23
Volume:	528.377
LogP:	6.685
LogD:	3.525
LogS:	-2.604
# Rotatable Bonds:	6
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	3.936
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.809
MDCK Permeability:	1.3543087334255688e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.214
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.528
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	95.8533706665039%
Volume Distribution (VD):	0.686
Pgp-substrate:	4.689997673034668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.277
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	5.822
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.817
Carcinogencity:	0.196
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.744

Download Data

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

Natural Product: NPC281137

Natural Product ID:	NPC281137
*Common Name:**	Dorsilurin I
IUPAC Name:	3,5-dihydroxy-2-[3-hydroxy-4-[(2S)-2-hydroxy-3-methylbut-3-enyl]phenyl]-8,8-dimethyl-6-(3-methylbut-2-enyl)-9,10-dihydropyrano[2,3-h]chromen-4-one
Synonyms:	dorsilurin I
Standard InCHIKey:	LGOMXMSCNFANHV-NRFANRHFSA-N
Standard InCHI:	InChI=1S/C30H34O7/c1-15(2)7-10-19-24(33)23-25(34)26(35)27(36-29(23)20-11-12-30(5,6)37-28(19)20)18-9-8-17(22(32)14-18)13-21(31)16(3)4/h7-9,14,21,31-33,35H,3,10-13H2,1-2,4-6H3/t21-/m0/s1
SMILES:	CC(=CCc1c(c2c(=O)c(c(c3ccc(C[C@@H](C(=C)C)O)c(c3)O)oc2c2CCC(C)(C)Oc12)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489470
PubChem CID:	25178184
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	21490.0	nM	PMID[520478]
NPT2	Others	Unspecified		IC50	=	431140.0	nM	PMID[520478]

☑ 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 NPC281137 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	438
0.1-0.2	1631
0.2-0.3	3972
0.3-0.4	9605
0.4-0.5	8709
0.5-0.6	3768
0.6-0.7	5146
0.7-0.8	4747
0.8-0.85	2525
0.85-0.9	1741
0.9-0.95	406
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282390
0.9799	High Similarity	NPC193200
0.9732	High Similarity	NPC142527
0.9603	High Similarity	NPC275575
0.96	High Similarity	NPC45934
0.9597	High Similarity	NPC472633
0.953	High Similarity	NPC269420
0.9474	High Similarity	NPC48579
0.9474	High Similarity	NPC259710
0.9474	High Similarity	NPC304207
0.9474	High Similarity	NPC217706
0.9474	High Similarity	NPC207809
0.9467	High Similarity	NPC61258
0.9463	High Similarity	NPC296869
0.9408	High Similarity	NPC248793
0.9408	High Similarity	NPC311579
0.9408	High Similarity	NPC180301
0.9408	High Similarity	NPC236756
0.94	High Similarity	NPC5173
0.9396	High Similarity	NPC473077
0.9396	High Similarity	NPC283234
0.9396	High Similarity	NPC296998
0.9346	High Similarity	NPC111341
0.9346	High Similarity	NPC304745
0.9342	High Similarity	NPC138288
0.9338	High Similarity	NPC37348
0.9333	High Similarity	NPC132592
0.9333	High Similarity	NPC160821
0.9333	High Similarity	NPC244407
0.9329	High Similarity	NPC111786
0.9329	High Similarity	NPC290133
0.9329	High Similarity	NPC195621
0.9329	High Similarity	NPC187282
0.9329	High Similarity	NPC20488
0.9329	High Similarity	NPC472629
0.9329	High Similarity	NPC176229
0.9329	High Similarity	NPC470647
0.9329	High Similarity	NPC267375
0.9329	High Similarity	NPC214774
0.9329	High Similarity	NPC88964
0.9329	High Similarity	NPC142405
0.9329	High Similarity	NPC312973
0.9329	High Similarity	NPC24136
0.9329	High Similarity	NPC475052
0.9329	High Similarity	NPC54577
0.9329	High Similarity	NPC83357
0.9329	High Similarity	NPC124729
0.9329	High Similarity	NPC246948
0.9329	High Similarity	NPC67805
0.9329	High Similarity	NPC301276
0.9299	High Similarity	NPC472625
0.9286	High Similarity	NPC215917
0.9286	High Similarity	NPC20530
0.9286	High Similarity	NPC10754
0.9281	High Similarity	NPC169990
0.9281	High Similarity	NPC293286
0.9281	High Similarity	NPC223701
0.9281	High Similarity	NPC472583
0.9281	High Similarity	NPC7989
0.9281	High Similarity	NPC210942
0.9281	High Similarity	NPC268193
0.9276	High Similarity	NPC278476
0.9276	High Similarity	NPC319910
0.9276	High Similarity	NPC262038
0.9276	High Similarity	NPC262039
0.9276	High Similarity	NPC254412
0.9276	High Similarity	NPC471677
0.9272	High Similarity	NPC474052
0.9272	High Similarity	NPC470461
0.9267	High Similarity	NPC23728
0.9267	High Similarity	NPC166757
0.9267	High Similarity	NPC14001
0.9267	High Similarity	NPC110303
0.9262	High Similarity	NPC470890
0.9262	High Similarity	NPC124780
0.9262	High Similarity	NPC273538
0.9262	High Similarity	NPC224714
0.9262	High Similarity	NPC216538
0.9262	High Similarity	NPC87486
0.9231	High Similarity	NPC475784
0.9226	High Similarity	NPC473272
0.9226	High Similarity	NPC284820
0.9221	High Similarity	NPC477958
0.9221	High Similarity	NPC476169
0.9216	High Similarity	NPC244583
0.9216	High Similarity	NPC475790
0.9216	High Similarity	NPC217149
0.9216	High Similarity	NPC10807
0.9216	High Similarity	NPC150123
0.9216	High Similarity	NPC171651
0.9216	High Similarity	NPC35567
0.9216	High Similarity	NPC216035
0.9216	High Similarity	NPC161881
0.9216	High Similarity	NPC56232
0.9216	High Similarity	NPC243171
0.9211	High Similarity	NPC29777
0.9211	High Similarity	NPC105136
0.9211	High Similarity	NPC471115
0.9205	High Similarity	NPC470460
0.9205	High Similarity	NPC6511
0.9205	High Similarity	NPC161191
0.92	High Similarity	NPC5820
0.92	High Similarity	NPC196114
0.92	High Similarity	NPC220418
0.92	High Similarity	NPC285630
0.92	High Similarity	NPC178343
0.92	High Similarity	NPC470458
0.92	High Similarity	NPC306488
0.92	High Similarity	NPC127059
0.9195	High Similarity	NPC24821
0.9195	High Similarity	NPC190637
0.9195	High Similarity	NPC185276
0.9195	High Similarity	NPC9117
0.9195	High Similarity	NPC219915
0.9195	High Similarity	NPC478086
0.9195	High Similarity	NPC316816
0.9195	High Similarity	NPC214166
0.9195	High Similarity	NPC212932
0.9195	High Similarity	NPC293053
0.9182	High Similarity	NPC471213
0.9172	High Similarity	NPC289771
0.9172	High Similarity	NPC474038
0.9172	High Similarity	NPC3629
0.9167	High Similarity	NPC22192
0.9161	High Similarity	NPC208152
0.9161	High Similarity	NPC78492
0.9156	High Similarity	NPC329844
0.9156	High Similarity	NPC244250
0.9156	High Similarity	NPC100134
0.9156	High Similarity	NPC469405
0.9156	High Similarity	NPC88983
0.9156	High Similarity	NPC209760
0.9156	High Similarity	NPC20907
0.915	High Similarity	NPC472420
0.915	High Similarity	NPC263384
0.915	High Similarity	NPC232645
0.915	High Similarity	NPC478148
0.915	High Similarity	NPC328740
0.915	High Similarity	NPC244577
0.915	High Similarity	NPC289774
0.915	High Similarity	NPC471676
0.915	High Similarity	NPC474023
0.915	High Similarity	NPC472422
0.915	High Similarity	NPC209846
0.915	High Similarity	NPC477897
0.915	High Similarity	NPC72958
0.915	High Similarity	NPC474021
0.9145	High Similarity	NPC472628
0.9145	High Similarity	NPC473016
0.9139	High Similarity	NPC97716
0.9139	High Similarity	NPC237635
0.9139	High Similarity	NPC201731
0.9139	High Similarity	NPC104406
0.9139	High Similarity	NPC24673
0.9139	High Similarity	NPC472627
0.9139	High Similarity	NPC79469
0.9133	High Similarity	NPC131579
0.9133	High Similarity	NPC235217
0.9133	High Similarity	NPC319752
0.9133	High Similarity	NPC197252
0.9133	High Similarity	NPC236766
0.9133	High Similarity	NPC473014
0.9133	High Similarity	NPC209040
0.9133	High Similarity	NPC326500
0.9133	High Similarity	NPC131568
0.9128	High Similarity	NPC1089
0.9128	High Similarity	NPC473042
0.9128	High Similarity	NPC10937
0.9128	High Similarity	NPC328164
0.9128	High Similarity	NPC220998
0.9128	High Similarity	NPC228504
0.9128	High Similarity	NPC32739
0.9128	High Similarity	NPC265040
0.9128	High Similarity	NPC166482
0.9128	High Similarity	NPC227579
0.9128	High Similarity	NPC64915
0.9128	High Similarity	NPC324436
0.9128	High Similarity	NPC324134
0.9128	High Similarity	NPC223500
0.9128	High Similarity	NPC296917
0.9128	High Similarity	NPC107572
0.9128	High Similarity	NPC66515
0.9128	High Similarity	NPC37496
0.9128	High Similarity	NPC182852
0.9128	High Similarity	NPC161506
0.9128	High Similarity	NPC78
0.9128	High Similarity	NPC76338
0.9128	High Similarity	NPC40833
0.9128	High Similarity	NPC306829
0.9128	High Similarity	NPC76372
0.9128	High Similarity	NPC166934
0.9128	High Similarity	NPC125855
0.9128	High Similarity	NPC167624
0.9128	High Similarity	NPC200694
0.9128	High Similarity	NPC177354
0.9128	High Similarity	NPC194432
0.9128	High Similarity	NPC148757
0.9128	High Similarity	NPC73028
0.9125	High Similarity	NPC218226
0.9108	High Similarity	NPC471976

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 NPC281137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	933
0.2-0.3	1802
0.3-0.4	2632
0.4-0.5	1855
0.5-0.6	975
0.6-0.7	381
0.7-0.8	131
0.8-0.85	32
0.85-0.9	26
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9262	High Similarity	NPD4378	Clinical (unspecified phase)
0.9032	High Similarity	NPD2393	Clinical (unspecified phase)
0.8961	High Similarity	NPD4380	Phase 2
0.8861	High Similarity	NPD7075	Discontinued
0.8854	High Similarity	NPD8443	Clinical (unspecified phase)
0.8834	High Similarity	NPD7804	Clinical (unspecified phase)
0.8812	High Similarity	NPD6959	Discontinued
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.879	High Similarity	NPD7096	Clinical (unspecified phase)
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.8758	High Similarity	NPD7410	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8726	High Similarity	NPD1934	Approved
0.8671	High Similarity	NPD7819	Suspended
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8608	High Similarity	NPD6801	Discontinued
0.86	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD1512	Approved
0.8563	High Similarity	NPD7251	Discontinued
0.8544	High Similarity	NPD7411	Suspended
0.8533	High Similarity	NPD1510	Phase 2
0.8512	High Similarity	NPD7808	Phase 3
0.8503	High Similarity	NPD6797	Phase 2
0.8494	Intermediate Similarity	NPD7054	Approved
0.8452	Intermediate Similarity	NPD1511	Approved
0.8443	Intermediate Similarity	NPD7472	Approved
0.8443	Intermediate Similarity	NPD7074	Phase 3
0.8438	Intermediate Similarity	NPD2801	Approved
0.84	Intermediate Similarity	NPD1607	Approved
0.8385	Intermediate Similarity	NPD3817	Phase 2
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5494	Approved
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8272	Intermediate Similarity	NPD5402	Approved
0.8267	Intermediate Similarity	NPD1240	Approved
0.825	Intermediate Similarity	NPD6599	Discontinued
0.8221	Intermediate Similarity	NPD7768	Phase 2
0.8217	Intermediate Similarity	NPD6799	Approved
0.8214	Intermediate Similarity	NPD3818	Discontinued
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5403	Approved
0.8165	Intermediate Similarity	NPD2534	Approved
0.8165	Intermediate Similarity	NPD2533	Approved
0.8165	Intermediate Similarity	NPD2532	Approved
0.8155	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD6100	Approved
0.8117	Intermediate Similarity	NPD6099	Approved
0.811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6232	Discontinued
0.805	Intermediate Similarity	NPD5401	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2800	Approved
0.7952	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7390	Discontinued
0.7874	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3226	Approved
0.784	Intermediate Similarity	NPD920	Approved
0.7834	Intermediate Similarity	NPD2346	Discontinued
0.7833	Intermediate Similarity	NPD4363	Phase 3
0.7833	Intermediate Similarity	NPD4360	Phase 2
0.7826	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1247	Approved
0.7806	Intermediate Similarity	NPD6651	Approved
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7798	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7286	Phase 2
0.7744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5124	Phase 1
0.7736	Intermediate Similarity	NPD1243	Approved
0.7727	Intermediate Similarity	NPD8313	Approved
0.7727	Intermediate Similarity	NPD8312	Approved
0.7717	Intermediate Similarity	NPD6776	Approved
0.7717	Intermediate Similarity	NPD6780	Approved
0.7717	Intermediate Similarity	NPD6781	Approved
0.7717	Intermediate Similarity	NPD6782	Approved
0.7717	Intermediate Similarity	NPD6779	Approved
0.7717	Intermediate Similarity	NPD6777	Approved
0.7717	Intermediate Similarity	NPD6778	Approved
0.7716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4625	Phase 3
0.7707	Intermediate Similarity	NPD3748	Approved
0.7707	Intermediate Similarity	NPD7033	Discontinued
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD7435	Discontinued
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7696	Phase 3
0.7688	Intermediate Similarity	NPD7697	Approved
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7688	Intermediate Similarity	NPD7698	Approved
0.7662	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7661	Intermediate Similarity	NPD5710	Approved
0.7661	Intermediate Similarity	NPD5711	Approved
0.7657	Intermediate Similarity	NPD5953	Discontinued
0.7647	Intermediate Similarity	NPD7870	Phase 2
0.7647	Intermediate Similarity	NPD7871	Phase 2
0.7647	Intermediate Similarity	NPD4908	Phase 1
0.7605	Intermediate Similarity	NPD6844	Discontinued
0.7595	Intermediate Similarity	NPD2799	Discontinued
0.7566	Intermediate Similarity	NPD7584	Approved
0.7564	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1613	Approved
0.7545	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7701	Phase 2
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD4308	Phase 3
0.7456	Intermediate Similarity	NPD1465	Phase 2
0.7452	Intermediate Similarity	NPD943	Approved
0.7448	Intermediate Similarity	NPD7874	Approved
0.7448	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6534	Approved
0.7446	Intermediate Similarity	NPD6535	Approved
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4749	Approved
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD7700	Phase 2
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7419	Intermediate Similarity	NPD7699	Phase 2
0.7418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7409	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7783	Phase 2
0.7409	Intermediate Similarity	NPD7801	Approved
0.7405	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4361	Phase 2
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7383	Intermediate Similarity	NPD1548	Phase 1
0.7356	Intermediate Similarity	NPD7229	Phase 3
0.7354	Intermediate Similarity	NPD6823	Phase 2
0.7353	Intermediate Similarity	NPD5761	Phase 2
0.7353	Intermediate Similarity	NPD5760	Phase 2
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD5406	Approved
0.7329	Intermediate Similarity	NPD5408	Approved
0.7329	Intermediate Similarity	NPD5405	Approved
0.7329	Intermediate Similarity	NPD5404	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2798	Approved
0.7277	Intermediate Similarity	NPD8320	Phase 1
0.7277	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3027	Phase 3
0.7251	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD6273	Approved
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7233	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD2797	Approved
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD411	Approved
0.7212	Intermediate Similarity	NPD6190	Approved
0.7202	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD37	Approved
0.7191	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7177	Discontinued
0.7191	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD230	Phase 1
0.7178	Intermediate Similarity	NPD1471	Phase 3
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4966	Approved
0.7165	Intermediate Similarity	NPD7585	Approved
0.7161	Intermediate Similarity	NPD3225	Approved
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7135	Intermediate Similarity	NPD5889	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