NPASS Compound

Structure

NPC110776 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 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 2.5981 -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 1.7321 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -0.0000 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 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 -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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 11 15 1 0 0 0 0 11 16 2 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 13 10 1 1 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 17 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	4.201
LogD:	2.308
LogS:	-3.877
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.833
Synthetic Accessibility Score:	3.147
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.893
MDCK Permeability:	1.3971304724691436e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	98.3541030883789%
Volume Distribution (VD):	0.505
Pgp-substrate:	1.3853647708892822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.487
CYP1A2-substrate:	0.229
CYP2C19-inhibitor:	0.62
CYP2C19-substrate:	0.265
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.339
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.41
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	3.865
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.702
Skin Sensitization:	0.839
Carcinogencity:	0.831
Eye Corrosion:	0.006
Eye Irritation:	0.913
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC110776

Natural Product ID:	NPC110776
*Common Name:**	(S)-5,7-Dihydroxy-8-Methyl-4-Oxo-2-Phenyl-Chroman-6-Carbaldehyde
IUPAC Name:	(2S)-5,7-dihydroxy-8-methyl-4-oxo-2-phenyl-2,3-dihydrochromene-6-carbaldehyde
Synonyms:
Standard InCHIKey:	OPZHOLABNKMTHG-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-9-15(20)11(8-18)16(21)14-12(19)7-13(22-17(9)14)10-5-3-2-4-6-10/h2-6,8,13,20-21H,7H2,1H3/t13-/m0/s1
SMILES:	Cc1c(c(C=O)c(c2C(=O)C[C@@H](c3ccccc3)Oc12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL53757
PubChem CID:	503267
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] 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
NPO33071	desmos spp.	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12729671]

☑ 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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	104.0	ug.mL-1	PMID[528107]
NPT759	Cell Line	H9	Homo sapiens	EC50	=	2.3	ug.mL-1	PMID[528107]
NPT27	Others	Unspecified		Therapeutic index	=	45.2	n.a.	PMID[528107]

☑ 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 NPC110776 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	361
0.1-0.2	1601
0.2-0.3	4143
0.3-0.4	10760
0.4-0.5	7630
0.5-0.6	3972
0.6-0.7	5919
0.7-0.8	5104
0.8-0.85	1752
0.85-0.9	1010
0.9-0.95	389
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271590
0.9928	High Similarity	NPC2416
0.9928	High Similarity	NPC476153
0.9928	High Similarity	NPC215885
0.9718	High Similarity	NPC214493
0.9643	High Similarity	NPC471621
0.964	High Similarity	NPC213322
0.964	High Similarity	NPC4743
0.964	High Similarity	NPC312391
0.964	High Similarity	NPC110038
0.964	High Similarity	NPC248372
0.964	High Similarity	NPC324386
0.9571	High Similarity	NPC177354
0.9571	High Similarity	NPC64915
0.9571	High Similarity	NPC265040
0.9571	High Similarity	NPC324436
0.9571	High Similarity	NPC220998
0.9571	High Similarity	NPC66515
0.9571	High Similarity	NPC227579
0.9571	High Similarity	NPC10937
0.9571	High Similarity	NPC328164
0.9571	High Similarity	NPC40833
0.9571	High Similarity	NPC76372
0.9571	High Similarity	NPC324134
0.9571	High Similarity	NPC148757
0.9571	High Similarity	NPC125855
0.9571	High Similarity	NPC37496
0.9571	High Similarity	NPC296917
0.9571	High Similarity	NPC1089
0.9571	High Similarity	NPC161506
0.9571	High Similarity	NPC194432
0.9571	High Similarity	NPC306829
0.9571	High Similarity	NPC76338
0.9571	High Similarity	NPC182852
0.9571	High Similarity	NPC166934
0.9571	High Similarity	NPC32739
0.9571	High Similarity	NPC107572
0.9571	High Similarity	NPC228504
0.9571	High Similarity	NPC167624
0.9571	High Similarity	NPC78
0.9571	High Similarity	NPC166482
0.9571	High Similarity	NPC223500
0.9504	High Similarity	NPC85162
0.9504	High Similarity	NPC223812
0.9504	High Similarity	NPC164980
0.9504	High Similarity	NPC125894
0.9504	High Similarity	NPC91560
0.9504	High Similarity	NPC316816
0.9504	High Similarity	NPC478086
0.9504	High Similarity	NPC185276
0.9504	High Similarity	NPC278249
0.9504	High Similarity	NPC175504
0.9504	High Similarity	NPC75049
0.9504	High Similarity	NPC107177
0.9504	High Similarity	NPC68104
0.9504	High Similarity	NPC214166
0.9504	High Similarity	NPC77794
0.9504	High Similarity	NPC221432
0.9504	High Similarity	NPC149026
0.9504	High Similarity	NPC81697
0.9504	High Similarity	NPC169591
0.9504	High Similarity	NPC257097
0.9504	High Similarity	NPC150408
0.9504	High Similarity	NPC39329
0.9504	High Similarity	NPC310130
0.9504	High Similarity	NPC143896
0.95	High Similarity	NPC279650
0.95	High Similarity	NPC22467
0.95	High Similarity	NPC96408
0.95	High Similarity	NPC156190
0.95	High Similarity	NPC17170
0.95	High Similarity	NPC258630
0.95	High Similarity	NPC3188
0.95	High Similarity	NPC166689
0.9496	High Similarity	NPC20709
0.9496	High Similarity	NPC274784
0.9496	High Similarity	NPC222342
0.9496	High Similarity	NPC265871
0.9496	High Similarity	NPC150648
0.9496	High Similarity	NPC225153
0.9496	High Similarity	NPC329203
0.9496	High Similarity	NPC310135
0.9437	High Similarity	NPC131568
0.9437	High Similarity	NPC235217
0.9437	High Similarity	NPC209040
0.9437	High Similarity	NPC473013
0.9437	High Similarity	NPC473015
0.9437	High Similarity	NPC473014
0.9437	High Similarity	NPC131579
0.9437	High Similarity	NPC197252
0.9437	High Similarity	NPC236766
0.9429	High Similarity	NPC188243
0.9429	High Similarity	NPC6407
0.9429	High Similarity	NPC110228
0.9371	High Similarity	NPC127059
0.9371	High Similarity	NPC312973
0.9371	High Similarity	NPC88964
0.9371	High Similarity	NPC470647
0.9371	High Similarity	NPC142405
0.9371	High Similarity	NPC470134
0.9371	High Similarity	NPC54577
0.9371	High Similarity	NPC475052
0.9371	High Similarity	NPC83357
0.9371	High Similarity	NPC473078
0.9371	High Similarity	NPC246948
0.9371	High Similarity	NPC67805
0.9371	High Similarity	NPC109183
0.9371	High Similarity	NPC301276
0.9371	High Similarity	NPC470133
0.9371	High Similarity	NPC470132
0.9371	High Similarity	NPC111786
0.9371	High Similarity	NPC195621
0.9371	High Similarity	NPC20488
0.9371	High Similarity	NPC472629
0.9371	High Similarity	NPC267375
0.9371	High Similarity	NPC176229
0.9371	High Similarity	NPC470131
0.9371	High Similarity	NPC285630
0.9371	High Similarity	NPC228779
0.9371	High Similarity	NPC214774
0.9357	High Similarity	NPC53181
0.9357	High Similarity	NPC18260
0.9357	High Similarity	NPC140890
0.9357	High Similarity	NPC78913
0.9357	High Similarity	NPC217186
0.9353	High Similarity	NPC13768
0.9353	High Similarity	NPC295261
0.9353	High Similarity	NPC12296
0.9353	High Similarity	NPC287246
0.9353	High Similarity	NPC79943
0.9353	High Similarity	NPC32441
0.9353	High Similarity	NPC107586
0.9353	High Similarity	NPC243083
0.9353	High Similarity	NPC296490
0.9306	High Similarity	NPC472627
0.9306	High Similarity	NPC300988
0.9306	High Similarity	NPC10990
0.9306	High Similarity	NPC283234
0.9306	High Similarity	NPC110303
0.9306	High Similarity	NPC296998
0.9306	High Similarity	NPC23728
0.9306	High Similarity	NPC473077
0.9301	High Similarity	NPC319752
0.9301	High Similarity	NPC271288
0.9301	High Similarity	NPC470890
0.9301	High Similarity	NPC470135
0.9301	High Similarity	NPC39045
0.9301	High Similarity	NPC87486
0.9301	High Similarity	NPC470136
0.9301	High Similarity	NPC124780
0.9296	High Similarity	NPC266725
0.9296	High Similarity	NPC147145
0.9291	High Similarity	NPC129853
0.9291	High Similarity	NPC241100
0.9291	High Similarity	NPC69769
0.9291	High Similarity	NPC76445
0.9291	High Similarity	NPC159275
0.9291	High Similarity	NPC284550
0.9286	High Similarity	NPC329225
0.9286	High Similarity	NPC472460
0.9286	High Similarity	NPC280284
0.9286	High Similarity	NPC99333
0.9286	High Similarity	NPC201395
0.9286	High Similarity	NPC118813
0.9286	High Similarity	NPC147686
0.9286	High Similarity	NPC471620
0.9286	High Similarity	NPC188947
0.9241	High Similarity	NPC160821
0.9241	High Similarity	NPC161191
0.9241	High Similarity	NPC132592
0.9236	High Similarity	NPC24136
0.9236	High Similarity	NPC290133
0.9236	High Similarity	NPC187282
0.9236	High Similarity	NPC474161
0.9236	High Similarity	NPC82534
0.9236	High Similarity	NPC476088
0.9231	High Similarity	NPC106985
0.9231	High Similarity	NPC166138
0.9231	High Similarity	NPC18585
0.9225	High Similarity	NPC282300
0.9225	High Similarity	NPC110969
0.922	High Similarity	NPC261234
0.922	High Similarity	NPC216978
0.922	High Similarity	NPC220062
0.922	High Similarity	NPC96565
0.922	High Similarity	NPC301217
0.922	High Similarity	NPC303633
0.922	High Similarity	NPC55018
0.9214	High Similarity	NPC84585
0.9214	High Similarity	NPC476480
0.9214	High Similarity	NPC290291
0.9214	High Similarity	NPC275055
0.9214	High Similarity	NPC259685
0.9189	High Similarity	NPC122365
0.9178	High Similarity	NPC164205
0.9178	High Similarity	NPC104236
0.9178	High Similarity	NPC19238
0.9178	High Similarity	NPC3642
0.9178	High Similarity	NPC473016
0.9178	High Similarity	NPC472628

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 NPC110776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	958
0.2-0.3	1577
0.3-0.4	2672
0.4-0.5	1885
0.5-0.6	1159
0.6-0.7	397
0.7-0.8	122
0.8-0.85	30
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9353	High Similarity	NPD1552	Clinical (unspecified phase)
0.9353	High Similarity	NPD1550	Clinical (unspecified phase)
0.9286	High Similarity	NPD1549	Phase 2
0.9128	High Similarity	NPD8443	Clinical (unspecified phase)
0.9054	High Similarity	NPD7411	Suspended
0.9034	High Similarity	NPD4378	Clinical (unspecified phase)
0.8933	High Similarity	NPD2393	Clinical (unspecified phase)
0.8904	High Similarity	NPD7410	Clinical (unspecified phase)
0.8803	High Similarity	NPD1510	Phase 2
0.8786	High Similarity	NPD1240	Approved
0.8758	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD1934	Approved
0.8741	High Similarity	NPD2796	Approved
0.8733	High Similarity	NPD4380	Phase 2
0.8684	High Similarity	NPD7096	Clinical (unspecified phase)
0.8662	High Similarity	NPD1607	Approved
0.8562	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD7421	Clinical (unspecified phase)
0.8544	High Similarity	NPD7852	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6801	Discontinued
0.8397	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD1511	Approved
0.8311	Intermediate Similarity	NPD2800	Approved
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1512	Approved
0.8217	Intermediate Similarity	NPD7768	Phase 2
0.8205	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6166	Phase 2
0.817	Intermediate Similarity	NPD920	Approved
0.8151	Intermediate Similarity	NPD6651	Approved
0.8146	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD6599	Discontinued
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6559	Discontinued
0.8101	Intermediate Similarity	NPD3882	Suspended
0.8063	Intermediate Similarity	NPD5494	Approved
0.805	Intermediate Similarity	NPD3749	Approved
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7947	Intermediate Similarity	NPD1243	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7935	Intermediate Similarity	NPD5403	Approved
0.7925	Intermediate Similarity	NPD3817	Phase 2
0.7922	Intermediate Similarity	NPD5401	Approved
0.7922	Intermediate Similarity	NPD2533	Approved
0.7922	Intermediate Similarity	NPD2532	Approved
0.7922	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD1247	Approved
0.7892	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD2313	Discontinued
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5953	Discontinued
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7834	Intermediate Similarity	NPD3226	Approved
0.7831	Intermediate Similarity	NPD7286	Phase 2
0.7815	Intermediate Similarity	NPD2344	Approved
0.78	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD3748	Approved
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD1203	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3268	Approved
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7746	Intermediate Similarity	NPD1610	Phase 2
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.774	Intermediate Similarity	NPD4908	Phase 1
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7718	Intermediate Similarity	NPD5124	Phase 1
0.7718	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1548	Phase 1
0.7711	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7682	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6099	Approved
0.7632	Intermediate Similarity	NPD6100	Approved
0.7625	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.7614	Intermediate Similarity	NPD4360	Phase 2
0.7614	Intermediate Similarity	NPD4363	Phase 3
0.7613	Intermediate Similarity	NPD2309	Approved
0.7593	Intermediate Similarity	NPD5402	Approved
0.7569	Intermediate Similarity	NPD9717	Approved
0.7534	Intermediate Similarity	NPD3267	Approved
0.7534	Intermediate Similarity	NPD3266	Approved
0.7533	Intermediate Similarity	NPD943	Approved
0.7516	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3225	Approved
0.7436	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5711	Approved
0.7425	Intermediate Similarity	NPD5710	Approved
0.7417	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1613	Approved
0.7415	Intermediate Similarity	NPD2797	Approved
0.7405	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4361	Phase 2
0.7374	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2654	Approved
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD2798	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6585	Discontinued
0.7343	Intermediate Similarity	NPD9545	Approved
0.7338	Intermediate Similarity	NPD4308	Phase 3
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7211	Intermediate Similarity	NPD1608	Approved
0.7211	Intermediate Similarity	NPD3972	Approved
0.7207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9493	Approved
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4287	Approved
0.7184	Intermediate Similarity	NPD6104	Discontinued
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7171	Intermediate Similarity	NPD1296	Phase 2
0.7169	Intermediate Similarity	NPD4288	Approved
0.7166	Intermediate Similarity	NPD7584	Approved
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.7118	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD5760	Phase 2
0.7108	Intermediate Similarity	NPD5761	Phase 2
0.7103	Intermediate Similarity	NPD1894	Discontinued
0.7102	Intermediate Similarity	NPD8313	Approved
0.7102	Intermediate Similarity	NPD8312	Approved
0.7089	Intermediate Similarity	NPD2424	Discontinued
0.7086	Intermediate Similarity	NPD2861	Phase 2
0.7081	Intermediate Similarity	NPD7212	Phase 2
0.7081	Intermediate Similarity	NPD7213	Phase 3
0.7078	Intermediate Similarity	NPD4307	Phase 2
0.707	Intermediate Similarity	NPD5405	Approved
0.707	Intermediate Similarity	NPD5404	Approved
0.707	Intermediate Similarity	NPD5406	Approved
0.707	Intermediate Similarity	NPD5408	Approved
0.7067	Intermediate Similarity	NPD1164	Approved
0.7067	Intermediate Similarity	NPD1470	Approved
0.7066	Intermediate Similarity	NPD2296	Approved
0.7059	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD411	Approved
0.7048	Intermediate Similarity	NPD6844	Discontinued
0.7047	Intermediate Similarity	NPD4749	Approved
0.7044	Intermediate Similarity	NPD1652	Phase 2
0.7037	Intermediate Similarity	NPD4661	Approved
0.7037	Intermediate Similarity	NPD4662	Approved
0.7035	Intermediate Similarity	NPD2403	Approved
0.7035	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD447	Suspended
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7018	Intermediate Similarity	NPD6808	Phase 2
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7007	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7	Intermediate Similarity	NPD7003	Approved
0.6994	Remote Similarity	NPD5049	Phase 3
0.6993	Remote Similarity	NPD3027	Phase 3
0.698	Remote Similarity	NPD1481	Phase 2
0.6975	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD9494	Approved
0.6968	Remote Similarity	NPD3142	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