NPASS Compound

Structure

CID35150 OpenBabel06191715362D 26 29 0 0 1 0 0 0 0 0999 V2000 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 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 -1.7321 3.0000 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 4.3301 2.5000 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 -0.8660 2.5000 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 3.4641 -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 0.8660 -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 4.3301 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 1.7321 -0.0000 0.0000 C 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 1.5000 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 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 21 17 1 6 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.13
Volume:	369.508
LogP:	4.566
LogD:	3.956
LogS:	-5.611
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	2.844
Fsp3:	0.087
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.746
MDCK Permeability:	1.4655426639365032e-05
Pgp-inhibitor:	0.668
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	97.68741607666016%
Volume Distribution (VD):	0.645
Pgp-substrate:	0.8996917009353638%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.828
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	12.822
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.822
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.944
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.831
Skin Sensitization:	0.281
Carcinogencity:	0.723
Eye Corrosion:	0.006
Eye Irritation:	0.894
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC35150

Natural Product ID:	NPC35150
*Common Name:**	Communin A
IUPAC Name:	(2S)-7-hydroxy-2-phenyl-5-[(Z)-2-phenylethenyl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	ZPNXTAJKEFNJMW-GMGKOPGTSA-N
Standard InCHI:	InChI=1S/C23H18O3/c24-19-13-18(12-11-16-7-3-1-4-8-16)23-20(25)15-21(26-22(23)14-19)17-9-5-2-6-10-17/h1-14,21,24H,15H2/b12-11-/t21-/m0/s1
SMILES:	Oc1cc(/C=Cc2ccccc2)c2c(c1)O[C@@H](CC2=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554121
PubChem CID:	44233686
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO23276	Flavoparmelia euplecta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650094]
NPO23405	Sidnyum turbinatum	n.a.	n.a.	n.a.	n.a.	Mediterranean	n.a.	PMID[11430005]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572610]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23997	Adesmia boronioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20283	Croton ruizianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23276	Flavoparmelia euplecta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23951	Oxytropis muricata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23405	Sidnyum turbinatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4019	Anabaena laxa	Species	0stocaceae	Bacteria	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[507783]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[507783]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.13	ug.mL-1	PMID[507783]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	0.11	ug.mL-1	PMID[507783]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.0022	ug.mL-1	PMID[507783]

☑ 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 NPC35150 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	411
0.1-0.2	1762
0.2-0.3	3993
0.3-0.4	10597
0.4-0.5	7525
0.5-0.6	3576
0.6-0.7	5344
0.7-0.8	5510
0.8-0.85	2513
0.85-0.9	1271
0.9-0.95	190
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106328
0.94	High Similarity	NPC195167
0.9379	High Similarity	NPC17101
0.9379	High Similarity	NPC77903
0.9375	High Similarity	NPC470135
0.9375	High Similarity	NPC39045
0.9375	High Similarity	NPC470136
0.9371	High Similarity	NPC310340
0.9338	High Similarity	NPC184326
0.9338	High Similarity	NPC292863
0.9324	High Similarity	NPC474843
0.931	High Similarity	NPC109183
0.931	High Similarity	NPC470133
0.931	High Similarity	NPC473078
0.931	High Similarity	NPC470132
0.931	High Similarity	NPC470134
0.931	High Similarity	NPC470131
0.9276	High Similarity	NPC18380
0.9276	High Similarity	NPC137232
0.9257	High Similarity	NPC148945
0.9257	High Similarity	NPC178484
0.9257	High Similarity	NPC72958
0.9257	High Similarity	NPC316960
0.9257	High Similarity	NPC204561
0.9257	High Similarity	NPC317715
0.9257	High Similarity	NPC78835
0.9257	High Similarity	NPC232645
0.9257	High Similarity	NPC309512
0.9236	High Similarity	NPC73028
0.9231	High Similarity	NPC188243
0.9231	High Similarity	NPC182421
0.9231	High Similarity	NPC6407
0.9231	High Similarity	NPC275734
0.9231	High Similarity	NPC110228
0.92	High Similarity	NPC67396
0.9195	High Similarity	NPC87708
0.9189	High Similarity	NPC472633
0.9184	High Similarity	NPC122894
0.9178	High Similarity	NPC290133
0.9178	High Similarity	NPC187282
0.9178	High Similarity	NPC24136
0.9178	High Similarity	NPC228779
0.9167	High Similarity	NPC96692
0.9161	High Similarity	NPC274784
0.9161	High Similarity	NPC222342
0.9161	High Similarity	NPC310135
0.9161	High Similarity	NPC316480
0.9161	High Similarity	NPC20709
0.9161	High Similarity	NPC265871
0.9161	High Similarity	NPC140890
0.9161	High Similarity	NPC329203
0.9161	High Similarity	NPC150648
0.9161	High Similarity	NPC225153
0.9156	High Similarity	NPC290160
0.9155	High Similarity	NPC287246
0.9155	High Similarity	NPC295261
0.9155	High Similarity	NPC32441
0.9155	High Similarity	NPC79943
0.9155	High Similarity	NPC296490
0.9155	High Similarity	NPC84585
0.9155	High Similarity	NPC243083
0.9155	High Similarity	NPC476480
0.9155	High Similarity	NPC13768
0.9155	High Similarity	NPC107586
0.9155	High Similarity	NPC12296
0.9139	High Similarity	NPC24640
0.9139	High Similarity	NPC208152
0.9139	High Similarity	NPC78492
0.9133	High Similarity	NPC329844
0.9133	High Similarity	NPC121568
0.9128	High Similarity	NPC478148
0.9128	High Similarity	NPC474417
0.9128	High Similarity	NPC149526
0.9122	High Similarity	NPC3642
0.9122	High Similarity	NPC473978
0.9122	High Similarity	NPC473016
0.9116	High Similarity	NPC10990
0.9116	High Similarity	NPC296998
0.9116	High Similarity	NPC473077
0.9116	High Similarity	NPC300988
0.911	High Similarity	NPC311144
0.911	High Similarity	NPC271288
0.9103	High Similarity	NPC1089
0.9103	High Similarity	NPC328164
0.9103	High Similarity	NPC166934
0.9103	High Similarity	NPC10937
0.9103	High Similarity	NPC32739
0.9103	High Similarity	NPC265040
0.9103	High Similarity	NPC227579
0.9103	High Similarity	NPC64915
0.9103	High Similarity	NPC324436
0.9103	High Similarity	NPC223500
0.9103	High Similarity	NPC324134
0.9103	High Similarity	NPC66515
0.9103	High Similarity	NPC182852
0.9103	High Similarity	NPC161506
0.9103	High Similarity	NPC296917
0.9103	High Similarity	NPC107572
0.9103	High Similarity	NPC37496
0.9103	High Similarity	NPC78
0.9103	High Similarity	NPC166482
0.9103	High Similarity	NPC306829
0.9103	High Similarity	NPC76338
0.9103	High Similarity	NPC177354
0.9103	High Similarity	NPC125855
0.9103	High Similarity	NPC40833
0.9103	High Similarity	NPC202981
0.9103	High Similarity	NPC220998
0.9103	High Similarity	NPC76372
0.9103	High Similarity	NPC167624
0.9103	High Similarity	NPC194432
0.9103	High Similarity	NPC148757
0.9103	High Similarity	NPC228504
0.9097	High Similarity	NPC284550
0.9097	High Similarity	NPC129853
0.9097	High Similarity	NPC76445
0.9091	High Similarity	NPC329225
0.9091	High Similarity	NPC472460
0.9091	High Similarity	NPC118813
0.9091	High Similarity	NPC147686
0.9073	High Similarity	NPC300668
0.9073	High Similarity	NPC182555
0.9073	High Similarity	NPC66441
0.9073	High Similarity	NPC254351
0.9073	High Similarity	NPC134171
0.9073	High Similarity	NPC258474
0.9073	High Similarity	NPC201227
0.9067	High Similarity	NPC40356
0.9067	High Similarity	NPC174086
0.9067	High Similarity	NPC154683
0.906	High Similarity	NPC227122
0.9048	High Similarity	NPC20488
0.9048	High Similarity	NPC83357
0.9048	High Similarity	NPC267375
0.9048	High Similarity	NPC111786
0.9048	High Similarity	NPC88964
0.9048	High Similarity	NPC301276
0.9048	High Similarity	NPC299011
0.9048	High Similarity	NPC214774
0.9048	High Similarity	NPC54577
0.9048	High Similarity	NPC472629
0.9048	High Similarity	NPC469758
0.9048	High Similarity	NPC196114
0.9048	High Similarity	NPC475052
0.9048	High Similarity	NPC67805
0.9048	High Similarity	NPC470647
0.9048	High Similarity	NPC246948
0.9048	High Similarity	NPC312973
0.9048	High Similarity	NPC195621
0.9048	High Similarity	NPC176229
0.9048	High Similarity	NPC142405
0.9041	High Similarity	NPC125894
0.9041	High Similarity	NPC81697
0.9041	High Similarity	NPC316816
0.9041	High Similarity	NPC77794
0.9041	High Similarity	NPC91560
0.9041	High Similarity	NPC75049
0.9041	High Similarity	NPC164980
0.9041	High Similarity	NPC113770
0.9041	High Similarity	NPC107177
0.9041	High Similarity	NPC175504
0.9041	High Similarity	NPC169591
0.9041	High Similarity	NPC68104
0.9041	High Similarity	NPC221432
0.9041	High Similarity	NPC150408
0.9041	High Similarity	NPC478086
0.9041	High Similarity	NPC278249
0.9041	High Similarity	NPC185276
0.9041	High Similarity	NPC149026
0.9041	High Similarity	NPC310130
0.9041	High Similarity	NPC223812
0.9041	High Similarity	NPC257097
0.9041	High Similarity	NPC39329
0.9041	High Similarity	NPC143896
0.9041	High Similarity	NPC214166
0.9041	High Similarity	NPC85162
0.9034	High Similarity	NPC258630
0.9034	High Similarity	NPC279650
0.9034	High Similarity	NPC4743
0.9034	High Similarity	NPC110038
0.9034	High Similarity	NPC324386
0.9034	High Similarity	NPC312391
0.9034	High Similarity	NPC213322
0.9034	High Similarity	NPC96408
0.9034	High Similarity	NPC14871
0.9034	High Similarity	NPC156190
0.9034	High Similarity	NPC17170
0.9034	High Similarity	NPC248372
0.9034	High Similarity	NPC166689
0.9034	High Similarity	NPC49108
0.9028	High Similarity	NPC261234
0.9026	High Similarity	NPC301256
0.9026	High Similarity	NPC312273
0.9021	High Similarity	NPC275055
0.9021	High Similarity	NPC290291
0.902	High Similarity	NPC55443
0.902	High Similarity	NPC18699
0.902	High Similarity	NPC210459
0.9013	High Similarity	NPC61112
0.9013	High Similarity	NPC32867

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 NPC35150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	988
0.2-0.3	1498
0.3-0.4	2613
0.4-0.5	1809
0.5-0.6	1132
0.6-0.7	491
0.7-0.8	152
0.8-0.85	39
0.85-0.9	17
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9155	High Similarity	NPD1550	Clinical (unspecified phase)
0.9155	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1549	Phase 2
0.9073	High Similarity	NPD8443	Clinical (unspecified phase)
0.9026	High Similarity	NPD6959	Discontinued
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8882	High Similarity	NPD7819	Suspended
0.8819	High Similarity	NPD2796	Approved
0.8816	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD1510	Phase 2
0.875	High Similarity	NPD7411	Suspended
0.8734	High Similarity	NPD6166	Phase 2
0.8734	High Similarity	NPD6167	Clinical (unspecified phase)
0.8734	High Similarity	NPD6168	Clinical (unspecified phase)
0.8725	High Similarity	NPD7410	Clinical (unspecified phase)
0.8725	High Similarity	NPD4378	Clinical (unspecified phase)
0.871	High Similarity	NPD3749	Approved
0.8684	High Similarity	NPD4380	Phase 2
0.8601	High Similarity	NPD1240	Approved
0.859	High Similarity	NPD4381	Clinical (unspecified phase)
0.8581	High Similarity	NPD3750	Approved
0.8533	High Similarity	NPD1511	Approved
0.8526	High Similarity	NPD4868	Clinical (unspecified phase)
0.85	High Similarity	NPD7852	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1607	Approved
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8446	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1512	Approved
0.8408	Intermediate Similarity	NPD7768	Phase 2
0.8397	Intermediate Similarity	NPD2801	Approved
0.8397	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5844	Phase 1
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8291	Intermediate Similarity	NPD3882	Suspended
0.8261	Intermediate Similarity	NPD6232	Discontinued
0.825	Intermediate Similarity	NPD5494	Approved
0.8243	Intermediate Similarity	NPD3748	Approved
0.8232	Intermediate Similarity	NPD7054	Approved
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8194	Intermediate Similarity	NPD4908	Phase 1
0.8188	Intermediate Similarity	NPD6099	Approved
0.8188	Intermediate Similarity	NPD6100	Approved
0.8182	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD3818	Discontinued
0.817	Intermediate Similarity	NPD6799	Approved
0.8146	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6797	Phase 2
0.8121	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2532	Approved
0.8117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2534	Approved
0.8117	Intermediate Similarity	NPD2533	Approved
0.8113	Intermediate Similarity	NPD3817	Phase 2
0.8101	Intermediate Similarity	NPD6801	Discontinued
0.8089	Intermediate Similarity	NPD6599	Discontinued
0.8084	Intermediate Similarity	NPD7251	Discontinued
0.8082	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.8052	Intermediate Similarity	NPD7390	Discontinued
0.8036	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5403	Approved
0.8013	Intermediate Similarity	NPD2344	Approved
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7976	Intermediate Similarity	NPD6559	Discontinued
0.7959	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1610	Phase 2
0.7958	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1465	Phase 2
0.7911	Intermediate Similarity	NPD3226	Approved
0.7908	Intermediate Similarity	NPD2800	Approved
0.7885	Intermediate Similarity	NPD5401	Approved
0.7844	Intermediate Similarity	NPD3751	Discontinued
0.7832	Intermediate Similarity	NPD1201	Approved
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7818	Intermediate Similarity	NPD3787	Discontinued
0.7806	Intermediate Similarity	NPD2309	Approved
0.7778	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD8313	Approved
0.7778	Intermediate Similarity	NPD2346	Discontinued
0.777	Intermediate Similarity	NPD4625	Phase 3
0.7756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD943	Approved
0.7719	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD5404	Approved
0.7712	Intermediate Similarity	NPD5408	Approved
0.7712	Intermediate Similarity	NPD5405	Approved
0.7712	Intermediate Similarity	NPD5406	Approved
0.7677	Intermediate Similarity	NPD1243	Approved
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3926	Phase 2
0.7658	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4287	Approved
0.7651	Intermediate Similarity	NPD7199	Phase 2
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7635	Intermediate Similarity	NPD2861	Phase 2
0.7632	Intermediate Similarity	NPD6651	Approved
0.7628	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1470	Approved
0.7619	Intermediate Similarity	NPD1203	Approved
0.7616	Intermediate Similarity	NPD1613	Approved
0.7616	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6273	Approved
0.7605	Intermediate Similarity	NPD5710	Approved
0.7605	Intermediate Similarity	NPD5711	Approved
0.7605	Intermediate Similarity	NPD7229	Phase 3
0.7602	Intermediate Similarity	NPD5953	Discontinued
0.76	Intermediate Similarity	NPD3764	Approved
0.7584	Intermediate Similarity	NPD4360	Phase 2
0.7584	Intermediate Similarity	NPD4363	Phase 3
0.7568	Intermediate Similarity	NPD2798	Approved
0.7562	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD920	Approved
0.7561	Intermediate Similarity	NPD4288	Approved
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD3268	Approved
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7177	Discontinued
0.7425	Intermediate Similarity	NPD919	Approved
0.7419	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6778	Approved
0.7377	Intermediate Similarity	NPD6782	Approved
0.7377	Intermediate Similarity	NPD6781	Approved
0.7377	Intermediate Similarity	NPD6777	Approved
0.7377	Intermediate Similarity	NPD6779	Approved
0.7377	Intermediate Similarity	NPD6776	Approved
0.7377	Intermediate Similarity	NPD6780	Approved
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD422	Phase 1
0.734	Intermediate Similarity	NPD8151	Discontinued
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7337	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD6844	Discontinued
0.7333	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD7577	Discontinued
0.7329	Intermediate Similarity	NPD17	Approved
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD3225	Approved
0.7312	Intermediate Similarity	NPD7871	Phase 2
0.7312	Intermediate Similarity	NPD7870	Phase 2
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4966	Approved
0.7297	Intermediate Similarity	NPD9717	Approved
0.7297	Intermediate Similarity	NPD3972	Approved
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7213	Phase 3
0.7267	Intermediate Similarity	NPD7212	Phase 2
0.7263	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7783	Phase 2
0.7258	Intermediate Similarity	NPD7696	Phase 3
0.7258	Intermediate Similarity	NPD7698	Approved
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7258	Intermediate Similarity	NPD7697	Approved
0.7257	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7458	Discontinued
0.7253	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4361	Phase 2
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7246	Intermediate Similarity	NPD2296	Approved
0.7239	Intermediate Similarity	NPD7427	Discontinued
0.7233	Intermediate Similarity	NPD2654	Approved
0.7226	Intermediate Similarity	NPD230	Phase 1
0.7225	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD7447	Phase 1
0.7222	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1471	Phase 3
0.72	Intermediate Similarity	NPD1876	Approved
0.7197	Intermediate Similarity	NPD4308	Phase 3
0.7192	Intermediate Similarity	NPD9545	Approved
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3027	Phase 3
0.7186	Intermediate Similarity	NPD5761	Phase 2
0.7186	Intermediate Similarity	NPD5760	Phase 2
0.7172	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD6971	Discontinued

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