NPASS Compound

Structure

CID193200 OpenBabel06191715582D 37 39 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -3.4641 -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 4.3301 1.5000 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -2.5981 -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 4.3301 2.5000 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 -0.8660 -1.5000 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 -1.7321 -2.0000 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 0.8660 -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 -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 2.5981 2.5000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 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 1 0 0 0 0 4 16 1 0 0 0 0 5 17 2 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 30 2 0 0 0 0 22 31 1 6 0 0 0 23 32 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 28 1 0 0 0 0 27 35 2 0 0 0 0 28 29 2 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.23
Volume:	534.297
LogP:	6.682
LogD:	3.057
LogS:	-3.197
# Rotatable Bonds:	8
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	3.893
Fsp3:	0.3
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:	-5.036
MDCK Permeability:	1.1382138836779632e-05
Pgp-inhibitor:	0.918
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.109
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	88.1015853881836%
Volume Distribution (VD):	0.863
Pgp-substrate:	11.531389236450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.314
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.209
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.747
CYP2C9-substrate:	0.501
CYP2D6-inhibitor:	0.258
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	7.922
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.86
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.254
Respiratory Toxicity:	0.655

Download Data

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

Natural Product: NPC193200

Natural Product ID:	NPC193200
*Common Name:**	Dorsilurin G
IUPAC Name:	3,5,7-trihydroxy-2-[3-hydroxy-4-[(2S)-2-hydroxy-3-methylbut-3-enyl]phenyl]-6,8-bis(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Dorsilurin G
Standard InCHIKey:	YIQFHSHQZCNILL-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C30H34O7/c1-15(2)7-11-20-25(33)21(12-8-16(3)4)30-24(26(20)34)27(35)28(36)29(37-30)19-10-9-18(23(32)14-19)13-22(31)17(5)6/h7-10,14,22,31-34,36H,5,11-13H2,1-4,6H3/t22-/m0/s1
SMILES:	CC(=CCc1c(c(CC=C(C)C)c2c(c1O)c(=O)c(c(c1ccc(C[C@@H](C(=C)C)O)c(c1)O)o2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489067
PubChem CID:	25181116
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.	root	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	n.a.	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	7510.0	nM	PMID[492556]
NPT2	Others	Unspecified	IC50	=	431140.0	nM	PMID[492556]
NPT2	Others	Unspecified	IC50	=	231990.0	nM	PMID[492556]

☑ 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 NPC193200 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	432
0.1-0.2	1619
0.2-0.3	4043
0.3-0.4	9627
0.4-0.5	8687
0.5-0.6	3568
0.6-0.7	5155
0.7-0.8	4781
0.8-0.85	2497
0.85-0.9	1754
0.9-0.95	526
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC281137
0.9799	High Similarity	NPC282390
0.9726	High Similarity	NPC269420
0.953	High Similarity	NPC45934
0.953	High Similarity	NPC142527
0.9527	High Similarity	NPC37348
0.9527	High Similarity	NPC61258
0.9459	High Similarity	NPC470461
0.9452	High Similarity	NPC216538
0.9452	High Similarity	NPC224714
0.9452	High Similarity	NPC273538
0.9404	High Similarity	NPC275575
0.94	High Similarity	NPC138288
0.9396	High Similarity	NPC472633
0.9392	High Similarity	NPC470460
0.9388	High Similarity	NPC290133
0.9388	High Similarity	NPC5820
0.9388	High Similarity	NPC472629
0.9388	High Similarity	NPC306488
0.9388	High Similarity	NPC124729
0.9388	High Similarity	NPC187282
0.9388	High Similarity	NPC470458
0.9388	High Similarity	NPC178343
0.9388	High Similarity	NPC24136
0.9384	High Similarity	NPC24821
0.9384	High Similarity	NPC293053
0.9384	High Similarity	NPC212932
0.9384	High Similarity	NPC190637
0.9384	High Similarity	NPC9117
0.9338	High Similarity	NPC169990
0.9338	High Similarity	NPC293286
0.9338	High Similarity	NPC210942
0.9333	High Similarity	NPC319910
0.9333	High Similarity	NPC254412
0.9333	High Similarity	NPC262038
0.9333	High Similarity	NPC278476
0.9333	High Similarity	NPC262039
0.9329	High Similarity	NPC5173
0.932	High Similarity	NPC326500
0.932	High Similarity	NPC87486
0.932	High Similarity	NPC470890
0.932	High Similarity	NPC124780
0.9315	High Similarity	NPC200694
0.9315	High Similarity	NPC473042
0.9276	High Similarity	NPC259710
0.9276	High Similarity	NPC304745
0.9276	High Similarity	NPC111341
0.9276	High Similarity	NPC304207
0.9276	High Similarity	NPC217706
0.9276	High Similarity	NPC48579
0.9276	High Similarity	NPC207809
0.9272	High Similarity	NPC217149
0.9272	High Similarity	NPC171651
0.9272	High Similarity	NPC216035
0.9272	High Similarity	NPC35567
0.9272	High Similarity	NPC243171
0.9267	High Similarity	NPC105136
0.9262	High Similarity	NPC168085
0.9262	High Similarity	NPC244407
0.9262	High Similarity	NPC296869
0.9252	High Similarity	NPC245482
0.9252	High Similarity	NPC117836
0.9252	High Similarity	NPC51887
0.9252	High Similarity	NPC476178
0.9252	High Similarity	NPC475705
0.9252	High Similarity	NPC185276
0.9252	High Similarity	NPC158874
0.9252	High Similarity	NPC301751
0.9221	High Similarity	NPC22192
0.9216	High Similarity	NPC20530
0.9216	High Similarity	NPC10754
0.9216	High Similarity	NPC215917
0.9211	High Similarity	NPC311579
0.9211	High Similarity	NPC268193
0.9211	High Similarity	NPC248793
0.9211	High Similarity	NPC236756
0.9211	High Similarity	NPC180301
0.9205	High Similarity	NPC471677
0.9205	High Similarity	NPC232645
0.9205	High Similarity	NPC478148
0.9205	High Similarity	NPC72958
0.92	High Similarity	NPC288036
0.92	High Similarity	NPC97029
0.92	High Similarity	NPC97028
0.92	High Similarity	NPC158338
0.92	High Similarity	NPC474052
0.92	High Similarity	NPC65589
0.92	High Similarity	NPC100985
0.92	High Similarity	NPC317492
0.9195	High Similarity	NPC296998
0.9195	High Similarity	NPC14001
0.9195	High Similarity	NPC166757
0.9195	High Similarity	NPC473077
0.9195	High Similarity	NPC283234
0.9189	High Similarity	NPC236766
0.9189	High Similarity	NPC235217
0.9189	High Similarity	NPC473014
0.9189	High Similarity	NPC319752
0.9189	High Similarity	NPC197252
0.9184	High Similarity	NPC32739
0.9184	High Similarity	NPC265040
0.9184	High Similarity	NPC227579
0.9184	High Similarity	NPC64915
0.9184	High Similarity	NPC223500
0.9184	High Similarity	NPC328164
0.9184	High Similarity	NPC10937
0.9184	High Similarity	NPC220998
0.9184	High Similarity	NPC66515
0.9184	High Similarity	NPC296917
0.9184	High Similarity	NPC324436
0.9184	High Similarity	NPC306829
0.9184	High Similarity	NPC324134
0.9184	High Similarity	NPC40833
0.9184	High Similarity	NPC148545
0.9184	High Similarity	NPC76372
0.9184	High Similarity	NPC125855
0.9184	High Similarity	NPC182852
0.9184	High Similarity	NPC161506
0.9184	High Similarity	NPC107572
0.9184	High Similarity	NPC37496
0.9184	High Similarity	NPC78
0.9184	High Similarity	NPC166934
0.9184	High Similarity	NPC166482
0.9184	High Similarity	NPC194432
0.9184	High Similarity	NPC148757
0.9184	High Similarity	NPC73028
0.9184	High Similarity	NPC76338
0.9184	High Similarity	NPC177354
0.9184	High Similarity	NPC1089
0.9184	High Similarity	NPC228504
0.9184	High Similarity	NPC167624
0.9178	High Similarity	NPC241100
0.9178	High Similarity	NPC159275
0.9161	High Similarity	NPC287328
0.9161	High Similarity	NPC282009
0.915	High Similarity	NPC321779
0.915	High Similarity	NPC226025
0.915	High Similarity	NPC133392
0.9145	High Similarity	NPC157784
0.9145	High Similarity	NPC161881
0.9145	High Similarity	NPC63187
0.9145	High Similarity	NPC87708
0.9145	High Similarity	NPC56232
0.9145	High Similarity	NPC10807
0.9145	High Similarity	NPC37684
0.9145	High Similarity	NPC150123
0.9145	High Similarity	NPC244583
0.9139	High Similarity	NPC321896
0.9139	High Similarity	NPC476185
0.9139	High Similarity	NPC202595
0.9139	High Similarity	NPC474735
0.9133	High Similarity	NPC27221
0.9133	High Similarity	NPC256672
0.9133	High Similarity	NPC7025
0.9133	High Similarity	NPC6511
0.9133	High Similarity	NPC145467
0.9133	High Similarity	NPC160821
0.9133	High Similarity	NPC132592
0.9133	High Similarity	NPC218569
0.9128	High Similarity	NPC301276
0.9128	High Similarity	NPC83357
0.9128	High Similarity	NPC214774
0.9128	High Similarity	NPC220418
0.9128	High Similarity	NPC469758
0.9128	High Similarity	NPC20488
0.9128	High Similarity	NPC475052
0.9128	High Similarity	NPC474161
0.9128	High Similarity	NPC312973
0.9128	High Similarity	NPC130176
0.9128	High Similarity	NPC285630
0.9128	High Similarity	NPC267375
0.9128	High Similarity	NPC54577
0.9128	High Similarity	NPC99454
0.9128	High Similarity	NPC142405
0.9128	High Similarity	NPC470647
0.9128	High Similarity	NPC476088
0.9128	High Similarity	NPC127059
0.9128	High Similarity	NPC246948
0.9128	High Similarity	NPC195621
0.9128	High Similarity	NPC67805
0.9128	High Similarity	NPC176229
0.9128	High Similarity	NPC196114
0.9128	High Similarity	NPC88964
0.9128	High Similarity	NPC111786
0.9122	High Similarity	NPC223812
0.9122	High Similarity	NPC68104
0.9122	High Similarity	NPC169591
0.9122	High Similarity	NPC257097
0.9122	High Similarity	NPC221432
0.9122	High Similarity	NPC278249
0.9122	High Similarity	NPC310130
0.9122	High Similarity	NPC214166
0.9122	High Similarity	NPC77794
0.9122	High Similarity	NPC107177
0.9122	High Similarity	NPC85162
0.9122	High Similarity	NPC164980
0.9122	High Similarity	NPC149026
0.9122	High Similarity	NPC175504
0.9122	High Similarity	NPC143896
0.9122	High Similarity	NPC81697

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 NPC193200 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	917
0.2-0.3	1777
0.3-0.4	2628
0.4-0.5	1872
0.5-0.6	979
0.6-0.7	403
0.7-0.8	135
0.8-0.85	35
0.85-0.9	21
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9452	High Similarity	NPD4378	Clinical (unspecified phase)
0.9085	High Similarity	NPD2393	Clinical (unspecified phase)
0.891	High Similarity	NPD7075	Discontinued
0.8889	High Similarity	NPD4380	Phase 2
0.8844	High Similarity	NPD1550	Clinical (unspecified phase)
0.8844	High Similarity	NPD1552	Clinical (unspecified phase)
0.8839	High Similarity	NPD7096	Clinical (unspecified phase)
0.8784	High Similarity	NPD1549	Phase 2
0.8782	High Similarity	NPD8443	Clinical (unspecified phase)
0.8776	High Similarity	NPD2796	Approved
0.8774	High Similarity	NPD1934	Approved
0.8774	High Similarity	NPD6801	Discontinued
0.8765	High Similarity	NPD7804	Clinical (unspecified phase)
0.875	High Similarity	NPD1512	Approved
0.8742	High Similarity	NPD6959	Discontinued
0.8718	High Similarity	NPD7819	Suspended
0.8707	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD6167	Clinical (unspecified phase)
0.8696	High Similarity	NPD6168	Clinical (unspecified phase)
0.8696	High Similarity	NPD6166	Phase 2
0.8684	High Similarity	NPD7410	Clinical (unspecified phase)
0.8618	High Similarity	NPD1511	Approved
0.8599	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD1607	Approved
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8544	High Similarity	NPD3817	Phase 2
0.8494	Intermediate Similarity	NPD7251	Discontinued
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8443	Intermediate Similarity	NPD7808	Phase 3
0.8435	Intermediate Similarity	NPD1240	Approved
0.8434	Intermediate Similarity	NPD6797	Phase 2
0.8424	Intermediate Similarity	NPD7054	Approved
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.8383	Intermediate Similarity	NPD6559	Discontinued
0.8377	Intermediate Similarity	NPD6799	Approved
0.8373	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD7074	Phase 3
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD2533	Approved
0.8323	Intermediate Similarity	NPD2534	Approved
0.8323	Intermediate Similarity	NPD2532	Approved
0.8313	Intermediate Similarity	NPD5402	Approved
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5494	Approved
0.8217	Intermediate Similarity	NPD5403	Approved
0.8204	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8133	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2800	Approved
0.8089	Intermediate Similarity	NPD5401	Approved
0.8065	Intermediate Similarity	NPD3750	Approved
0.8054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD6100	Approved
0.8039	Intermediate Similarity	NPD6099	Approved
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3226	Approved
0.7987	Intermediate Similarity	NPD920	Approved
0.7974	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6651	Approved
0.7955	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1247	Approved
0.7949	Intermediate Similarity	NPD4628	Phase 3
0.7939	Intermediate Similarity	NPD919	Approved
0.7911	Intermediate Similarity	NPD7390	Discontinued
0.7895	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1243	Approved
0.7882	Intermediate Similarity	NPD7286	Phase 2
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3749	Approved
0.7765	Intermediate Similarity	NPD4360	Phase 2
0.7765	Intermediate Similarity	NPD4363	Phase 3
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3748	Approved
0.7742	Intermediate Similarity	NPD7033	Discontinued
0.7742	Intermediate Similarity	NPD2799	Discontinued
0.7697	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5710	Approved
0.7692	Intermediate Similarity	NPD5711	Approved
0.7669	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8313	Approved
0.7657	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD3926	Phase 2
0.7643	Intermediate Similarity	NPD2344	Approved
0.7632	Intermediate Similarity	NPD4625	Phase 3
0.7597	Intermediate Similarity	NPD1613	Approved
0.7597	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD943	Approved
0.7582	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4908	Phase 1
0.7566	Intermediate Similarity	NPD6832	Phase 2
0.7554	Intermediate Similarity	NPD6777	Approved
0.7554	Intermediate Similarity	NPD6776	Approved
0.7554	Intermediate Similarity	NPD6780	Approved
0.7554	Intermediate Similarity	NPD6779	Approved
0.7554	Intermediate Similarity	NPD6778	Approved
0.7554	Intermediate Similarity	NPD6781	Approved
0.7554	Intermediate Similarity	NPD6782	Approved
0.7548	Intermediate Similarity	NPD5124	Phase 1
0.7548	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.753	Intermediate Similarity	NPD6844	Discontinued
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7528	Intermediate Similarity	NPD8150	Discontinued
0.7527	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7698	Approved
0.7527	Intermediate Similarity	NPD4361	Phase 2
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7453	Intermediate Similarity	NPD2309	Approved
0.745	Intermediate Similarity	NPD1610	Phase 2
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2798	Approved
0.7407	Intermediate Similarity	NPD7584	Approved
0.7403	Intermediate Similarity	NPD3027	Phase 3
0.7381	Intermediate Similarity	NPD1465	Phase 2
0.7381	Intermediate Similarity	NPD5760	Phase 2
0.7381	Intermediate Similarity	NPD5761	Phase 2
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7368	Intermediate Similarity	NPD2797	Approved
0.7366	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5408	Approved
0.7358	Intermediate Similarity	NPD5404	Approved
0.7358	Intermediate Similarity	NPD5406	Approved
0.7358	Intermediate Similarity	NPD5405	Approved
0.7355	Intermediate Similarity	NPD411	Approved
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7351	Intermediate Similarity	NPD4749	Approved
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1201	Approved
0.733	Intermediate Similarity	NPD8151	Discontinued
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6355	Discontinued
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7321	Intermediate Similarity	NPD37	Approved
0.7314	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1471	Phase 3
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD4965	Approved
0.7292	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD1608	Approved
0.7285	Intermediate Similarity	NPD3972	Approved
0.7283	Intermediate Similarity	NPD6534	Approved
0.7283	Intermediate Similarity	NPD6535	Approved
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7261	Intermediate Similarity	NPD4060	Phase 1
0.7261	Intermediate Similarity	NPD4307	Phase 2
0.7258	Intermediate Similarity	NPD7699	Phase 2
0.7258	Intermediate Similarity	NPD7700	Phase 2
0.7255	Intermediate Similarity	NPD1470	Approved
0.7254	Intermediate Similarity	NPD7783	Phase 2
0.7254	Intermediate Similarity	NPD7801	Approved
0.7254	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6190	Approved
0.7232	Intermediate Similarity	NPD1729	Discontinued
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7216	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD447	Suspended
0.7209	Intermediate Similarity	NPD6234	Discontinued
0.7208	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6233	Phase 2

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