NPASS Compound

Structure

CID185276 OpenBabel06191715562D 35 37 0 0 1 0 0 0 0 0999 V2000 8.6603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -5.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 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 6.9282 -2.0000 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 3.4641 -3.0000 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 -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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 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 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 -0.8660 -0.5000 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 -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 2.5981 -1.5000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 2 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 26 1 0 0 0 0 17 27 1 0 0 0 0 21 24 1 0 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 33 2 0 0 0 0 27 22 1 1 0 0 0 27 35 1 0 0 0 0 28 29 2 0 0 0 0 28 35 1 0 0 0 0 29 30 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.26
Volume:	519.353
LogP:	7.713
LogD:	4.621
LogS:	-2.929
# Rotatable Bonds:	8
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	3.678
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	2.037460399151314e-05
Pgp-inhibitor:	0.721
Pgp-substrate:	0.783
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.596

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.80299377441406%
Volume Distribution (VD):	1.133
Pgp-substrate:	2.527850866317749%

ADMET: Metabolism

CYP1A2-inhibitor:	0.361
CYP1A2-substrate:	0.357
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.811
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	13.028
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.643
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.918
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.829
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC185276

Natural Product ID:	NPC185276
*Common Name:**	Schizolaenone A
IUPAC Name:	(2S)-2-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-hydroxyphenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	NALIGSFHPZUJQO-KIAIXJHNSA-N
Standard InCHI:	InChI=1S/C30H36O5/c1-18(2)7-6-8-20(5)10-11-21-15-22(12-14-24(21)31)27-17-26(33)29-28(35-27)16-25(32)23(30(29)34)13-9-19(3)4/h7,9-10,12,14-16,27,31-32,34H,6,8,11,13,17H2,1-5H3/b20-10+/t27-/m0/s1
SMILES:	C/C(=CCc1cc(ccc1O)[C@@H]1CC(=O)c2c(O1)cc(c(c2O)CC=C(C)C)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516931
PubChem CID:	11420157
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[15787448]
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15787448]
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[546572]

☑ 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 NPC185276 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	355
0.1-0.2	1423
0.2-0.3	3515
0.3-0.4	9328
0.4-0.5	9366
0.5-0.6	3510
0.6-0.7	5703
0.7-0.8	5393
0.8-0.85	2143
0.85-0.9	1177
0.9-0.95	566
0.95-1	218

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC197252
0.9928	High Similarity	NPC235217
0.9928	High Similarity	NPC236766
0.9928	High Similarity	NPC473014
0.9927	High Similarity	NPC223500
0.9927	High Similarity	NPC220998
0.9927	High Similarity	NPC64915
0.9927	High Similarity	NPC66515
0.9927	High Similarity	NPC324134
0.9927	High Similarity	NPC177354
0.9927	High Similarity	NPC166482
0.9927	High Similarity	NPC194432
0.9927	High Similarity	NPC328164
0.9927	High Similarity	NPC148757
0.9927	High Similarity	NPC40833
0.9927	High Similarity	NPC76338
0.9927	High Similarity	NPC166934
0.9927	High Similarity	NPC296917
0.9927	High Similarity	NPC324436
0.9927	High Similarity	NPC265040
0.9927	High Similarity	NPC306829
0.9927	High Similarity	NPC10937
0.9927	High Similarity	NPC76372
0.9927	High Similarity	NPC125855
0.9927	High Similarity	NPC37496
0.9927	High Similarity	NPC182852
0.9927	High Similarity	NPC161506
0.9927	High Similarity	NPC228504
0.9927	High Similarity	NPC167624
0.9927	High Similarity	NPC107572
0.9927	High Similarity	NPC78
0.9927	High Similarity	NPC32739
0.9927	High Similarity	NPC1089
0.9927	High Similarity	NPC227579
0.9856	High Similarity	NPC285630
0.9856	High Similarity	NPC127059
0.9855	High Similarity	NPC85162
0.9855	High Similarity	NPC150408
0.9855	High Similarity	NPC164980
0.9855	High Similarity	NPC223812
0.9855	High Similarity	NPC214166
0.9855	High Similarity	NPC310130
0.9855	High Similarity	NPC107177
0.9855	High Similarity	NPC81697
0.9855	High Similarity	NPC75049
0.9855	High Similarity	NPC143896
0.9855	High Similarity	NPC221432
0.9855	High Similarity	NPC316816
0.9855	High Similarity	NPC125894
0.9855	High Similarity	NPC175504
0.9855	High Similarity	NPC169591
0.9855	High Similarity	NPC478086
0.9855	High Similarity	NPC149026
0.9855	High Similarity	NPC91560
0.9855	High Similarity	NPC77794
0.9855	High Similarity	NPC68104
0.9855	High Similarity	NPC257097
0.9855	High Similarity	NPC39329
0.9855	High Similarity	NPC278249
0.9854	High Similarity	NPC213322
0.9854	High Similarity	NPC110038
0.9854	High Similarity	NPC166689
0.9854	High Similarity	NPC324386
0.9854	High Similarity	NPC279650
0.9854	High Similarity	NPC17170
0.9854	High Similarity	NPC258630
0.9854	High Similarity	NPC96408
0.9854	High Similarity	NPC248372
0.9854	High Similarity	NPC156190
0.9854	High Similarity	NPC312391
0.9854	High Similarity	NPC4743
0.9786	High Similarity	NPC283234
0.9784	High Similarity	NPC209040
0.9784	High Similarity	NPC473013
0.9784	High Similarity	NPC131579
0.9784	High Similarity	NPC473015
0.9784	High Similarity	NPC131568
0.9781	High Similarity	NPC6407
0.9781	High Similarity	NPC110228
0.9781	High Similarity	NPC188243
0.9716	High Similarity	NPC160821
0.9716	High Similarity	NPC132592
0.9714	High Similarity	NPC54577
0.9714	High Similarity	NPC470132
0.9714	High Similarity	NPC470131
0.9714	High Similarity	NPC470134
0.9714	High Similarity	NPC176229
0.9714	High Similarity	NPC142405
0.9714	High Similarity	NPC214774
0.9714	High Similarity	NPC267375
0.9714	High Similarity	NPC109183
0.9714	High Similarity	NPC301276
0.9714	High Similarity	NPC312973
0.9714	High Similarity	NPC195621
0.9714	High Similarity	NPC20488
0.9714	High Similarity	NPC475052
0.9714	High Similarity	NPC472629
0.9714	High Similarity	NPC83357
0.9714	High Similarity	NPC67805
0.9714	High Similarity	NPC470133
0.9714	High Similarity	NPC246948
0.9714	High Similarity	NPC111786
0.9714	High Similarity	NPC88964
0.9714	High Similarity	NPC470647
0.9714	High Similarity	NPC473078
0.971	High Similarity	NPC3188
0.9708	High Similarity	NPC225153
0.9708	High Similarity	NPC150648
0.9708	High Similarity	NPC274784
0.9708	High Similarity	NPC329203
0.9708	High Similarity	NPC222342
0.9708	High Similarity	NPC265871
0.9708	High Similarity	NPC20709
0.9708	High Similarity	NPC140890
0.9708	High Similarity	NPC310135
0.9648	High Similarity	NPC472628
0.9645	High Similarity	NPC296998
0.9645	High Similarity	NPC473077
0.9645	High Similarity	NPC300988
0.9645	High Similarity	NPC472627
0.9645	High Similarity	NPC110303
0.9645	High Similarity	NPC23728
0.9645	High Similarity	NPC10990
0.9643	High Similarity	NPC470135
0.9643	High Similarity	NPC87486
0.9643	High Similarity	NPC124780
0.9643	High Similarity	NPC470136
0.9643	High Similarity	NPC271288
0.9643	High Similarity	NPC39045
0.9643	High Similarity	NPC319752
0.9643	High Similarity	NPC470890
0.964	High Similarity	NPC147145
0.9638	High Similarity	NPC284550
0.9638	High Similarity	NPC241100
0.9638	High Similarity	NPC69769
0.9638	High Similarity	NPC76445
0.9638	High Similarity	NPC159275
0.9638	High Similarity	NPC129853
0.9577	High Similarity	NPC145467
0.9577	High Similarity	NPC161191
0.9574	High Similarity	NPC2416
0.9574	High Similarity	NPC290133
0.9574	High Similarity	NPC474161
0.9574	High Similarity	NPC476153
0.9574	High Similarity	NPC228779
0.9574	High Similarity	NPC187282
0.9574	High Similarity	NPC24136
0.9574	High Similarity	NPC215885
0.9574	High Similarity	NPC476088
0.9571	High Similarity	NPC106985
0.9571	High Similarity	NPC471621
0.9571	High Similarity	NPC166138
0.9571	High Similarity	NPC18585
0.9568	High Similarity	NPC110969
0.9568	High Similarity	NPC282300
0.9565	High Similarity	NPC216978
0.9565	High Similarity	NPC55018
0.9565	High Similarity	NPC301217
0.9565	High Similarity	NPC303633
0.9565	High Similarity	NPC18260
0.9565	High Similarity	NPC78913
0.9565	High Similarity	NPC53181
0.9565	High Similarity	NPC217186
0.9565	High Similarity	NPC220062
0.9565	High Similarity	NPC96565
0.9562	High Similarity	NPC295261
0.9562	High Similarity	NPC107586
0.9562	High Similarity	NPC79943
0.9562	High Similarity	NPC12296
0.9562	High Similarity	NPC296490
0.9562	High Similarity	NPC13768
0.9562	High Similarity	NPC32441
0.9562	High Similarity	NPC259685
0.9562	High Similarity	NPC287246
0.9562	High Similarity	NPC243083
0.9514	High Similarity	NPC178484
0.9514	High Similarity	NPC471677
0.951	High Similarity	NPC3642
0.951	High Similarity	NPC473016
0.9507	High Similarity	NPC308200
0.9504	High Similarity	NPC110776
0.9504	High Similarity	NPC224714
0.9504	High Similarity	NPC271590
0.95	High Similarity	NPC11561
0.95	High Similarity	NPC266725
0.95	High Similarity	NPC226636
0.95	High Similarity	NPC144499
0.9496	High Similarity	NPC471587
0.9496	High Similarity	NPC172986
0.9496	High Similarity	NPC270883
0.9496	High Similarity	NPC261227
0.9496	High Similarity	NPC150522
0.9493	High Similarity	NPC124269
0.9493	High Similarity	NPC280284
0.9493	High Similarity	NPC99333
0.9493	High Similarity	NPC147686
0.9493	High Similarity	NPC329225
0.9493	High Similarity	NPC118813
0.9493	High Similarity	NPC472460
0.9493	High Similarity	NPC188947

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 NPC185276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	914
0.2-0.3	1509
0.3-0.4	2519
0.4-0.5	1979
0.5-0.6	1193
0.6-0.7	493
0.7-0.8	167
0.8-0.85	37
0.85-0.9	13
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9562	High Similarity	NPD1552	Clinical (unspecified phase)
0.9562	High Similarity	NPD1550	Clinical (unspecified phase)
0.9493	High Similarity	NPD1549	Phase 2
0.9366	High Similarity	NPD4378	Clinical (unspecified phase)
0.932	High Similarity	NPD8443	Clinical (unspecified phase)
0.9252	High Similarity	NPD2393	Clinical (unspecified phase)
0.9195	High Similarity	NPD7075	Discontinued
0.9122	High Similarity	NPD7096	Clinical (unspecified phase)
0.9116	High Similarity	NPD7411	Suspended
0.9097	High Similarity	NPD7410	Clinical (unspecified phase)
0.9071	High Similarity	NPD2796	Approved
0.9048	High Similarity	NPD4380	Phase 2
0.9	High Similarity	NPD1510	Phase 2
0.8993	High Similarity	NPD7819	Suspended
0.8986	High Similarity	NPD1240	Approved
0.8926	High Similarity	NPD1934	Approved
0.8857	High Similarity	NPD1607	Approved
0.88	High Similarity	NPD6801	Discontinued
0.8693	High Similarity	NPD4381	Clinical (unspecified phase)
0.8671	High Similarity	NPD7804	Clinical (unspecified phase)
0.8645	High Similarity	NPD6959	Discontinued
0.8639	High Similarity	NPD6799	Approved
0.8627	High Similarity	NPD7768	Phase 2
0.8621	High Similarity	NPD7421	Clinical (unspecified phase)
0.8599	High Similarity	NPD7852	Clinical (unspecified phase)
0.8571	High Similarity	NPD6859	Clinical (unspecified phase)
0.8514	High Similarity	NPD1511	Approved
0.8497	Intermediate Similarity	NPD2801	Approved
0.8481	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6166	Phase 2
0.8462	Intermediate Similarity	NPD6651	Approved
0.8421	Intermediate Similarity	NPD6599	Discontinued
0.84	Intermediate Similarity	NPD1512	Approved
0.8387	Intermediate Similarity	NPD3882	Suspended
0.8385	Intermediate Similarity	NPD7074	Phase 3
0.8367	Intermediate Similarity	NPD2800	Approved
0.8344	Intermediate Similarity	NPD5494	Approved
0.8323	Intermediate Similarity	NPD7054	Approved
0.8311	Intermediate Similarity	NPD3750	Approved
0.8288	Intermediate Similarity	NPD1551	Phase 2
0.8272	Intermediate Similarity	NPD7472	Approved
0.8224	Intermediate Similarity	NPD5403	Approved
0.8217	Intermediate Similarity	NPD3749	Approved
0.821	Intermediate Similarity	NPD7286	Phase 2
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8188	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7251	Discontinued
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.8163	Intermediate Similarity	NPD2935	Discontinued
0.8153	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8121	Intermediate Similarity	NPD7808	Phase 3
0.8121	Intermediate Similarity	NPD1243	Approved
0.8121	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6797	Phase 2
0.811	Intermediate Similarity	NPD5953	Discontinued
0.8105	Intermediate Similarity	NPD920	Approved
0.8095	Intermediate Similarity	NPD2799	Discontinued
0.8092	Intermediate Similarity	NPD2534	Approved
0.8092	Intermediate Similarity	NPD5401	Approved
0.8092	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD2532	Approved
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD4908	Phase 1
0.8042	Intermediate Similarity	NPD6832	Phase 2
0.8041	Intermediate Similarity	NPD6099	Approved
0.8041	Intermediate Similarity	NPD6100	Approved
0.8013	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD2344	Approved
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7033	Discontinued
0.7973	Intermediate Similarity	NPD3748	Approved
0.7958	Intermediate Similarity	NPD1203	Approved
0.7947	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD4628	Phase 3
0.7931	Intermediate Similarity	NPD2313	Discontinued
0.7929	Intermediate Similarity	NPD1610	Phase 2
0.7904	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1548	Phase 1
0.7891	Intermediate Similarity	NPD5124	Phase 1
0.7891	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5402	Approved
0.7861	Intermediate Similarity	NPD4363	Phase 3
0.7861	Intermediate Similarity	NPD4360	Phase 2
0.7852	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD2309	Approved
0.7771	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3226	Approved
0.7748	Intermediate Similarity	NPD2346	Discontinued
0.7746	Intermediate Similarity	NPD9717	Approved
0.7716	Intermediate Similarity	NPD919	Approved
0.7708	Intermediate Similarity	NPD2797	Approved
0.7703	Intermediate Similarity	NPD943	Approved
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7390	Discontinued
0.7676	Intermediate Similarity	NPD422	Phase 1
0.7655	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD2654	Approved
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD1729	Discontinued
0.7619	Intermediate Similarity	NPD4625	Phase 3
0.7614	Intermediate Similarity	NPD4361	Phase 2
0.7614	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1613	Approved
0.7576	Intermediate Similarity	NPD5710	Approved
0.7576	Intermediate Similarity	NPD5711	Approved
0.7568	Intermediate Similarity	NPD6798	Discontinued
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1933	Approved
0.753	Intermediate Similarity	NPD3926	Phase 2
0.7529	Intermediate Similarity	NPD6104	Discontinued
0.7518	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7486	Intermediate Similarity	NPD7584	Approved
0.747	Intermediate Similarity	NPD7229	Phase 3
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7466	Intermediate Similarity	NPD3267	Approved
0.7466	Intermediate Similarity	NPD3266	Approved
0.7453	Intermediate Similarity	NPD5889	Approved
0.7453	Intermediate Similarity	NPD5890	Approved
0.745	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8313	Approved
0.7442	Intermediate Similarity	NPD8312	Approved
0.7432	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6355	Discontinued
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD6844	Discontinued
0.7396	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1608	Approved
0.7376	Intermediate Similarity	NPD9493	Approved
0.7365	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2861	Phase 2
0.7362	Intermediate Similarity	NPD8455	Phase 2
0.7355	Intermediate Similarity	NPD2424	Discontinued
0.7342	Intermediate Similarity	NPD7213	Phase 3
0.7342	Intermediate Similarity	NPD7212	Phase 2
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7329	Intermediate Similarity	NPD4749	Approved
0.7317	Intermediate Similarity	NPD4288	Approved
0.731	Intermediate Similarity	NPD1201	Approved
0.7308	Intermediate Similarity	NPD1652	Phase 2
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7301	Intermediate Similarity	NPD7577	Discontinued
0.7297	Intermediate Similarity	NPD1019	Discontinued
0.7296	Intermediate Similarity	NPD7447	Phase 1
0.7296	Intermediate Similarity	NPD4662	Approved
0.7296	Intermediate Similarity	NPD4661	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6233	Phase 2
0.7284	Intermediate Similarity	NPD6585	Discontinued
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7261	Intermediate Similarity	NPD7003	Approved
0.7256	Intermediate Similarity	NPD5761	Phase 2
0.7256	Intermediate Similarity	NPD5760	Phase 2
0.7237	Intermediate Similarity	NPD3142	Approved
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.7237	Intermediate Similarity	NPD3140	Approved
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4287	Approved
0.7232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1470	Approved
0.723	Intermediate Similarity	NPD1164	Approved
0.7226	Intermediate Similarity	NPD5405	Approved
0.7226	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD5404	Approved
0.7226	Intermediate Similarity	NPD5406	Approved
0.7226	Intermediate Similarity	NPD4477	Approved
0.7226	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD3764	Approved
0.7219	Intermediate Similarity	NPD411	Approved
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7215	Intermediate Similarity	NPD3887	Approved
0.7212	Intermediate Similarity	NPD2296	Approved
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.719	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD6005	Phase 3
0.7179	Intermediate Similarity	NPD6004	Phase 3
0.7179	Intermediate Similarity	NPD1471	Phase 3
0.7179	Intermediate Similarity	NPD6002	Phase 3
0.7179	Intermediate Similarity	NPD6006	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data