NPASS Compound

Structure

NPC471621 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 2.5981 -0.5000 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 -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 -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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 3 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 -2.5981 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 10 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 19 2 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 11 1 6 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	319.711
LogP:	3.371
LogD:	2.248
LogS:	-3.817
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.852
Synthetic Accessibility Score:	3.503
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	1.2854227861680556e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.647
Plasma Protein Binding (PPB):	94.84634399414062%
Volume Distribution (VD):	1.046
Pgp-substrate:	3.2339227199554443%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.53
CYP2C19-inhibitor:	0.277
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.228
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.337
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.576

ADMET: Excretion

Clearance (CL):	7.535
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.778
Carcinogencity:	0.482
Eye Corrosion:	0.003
Eye Irritation:	0.623
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC471621

Natural Product ID:	NPC471621
*Common Name:**	(S)-4,7-Dihydroxy-5-Methoxy-6-Methyl-2-Phenyl-Chroman-8-Carbaldehyde
IUPAC Name:	(2S)-4,7-dihydroxy-5-methoxy-6-methyl-2-phenyl-3,4-dihydro-2H-chromene-8-carbaldehyde
Synonyms:
Standard InCHIKey:	DAAVAQORZATFQC-KZUDCZAMSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-10-16(21)12(9-19)18-15(17(10)22-2)13(20)8-14(23-18)11-6-4-3-5-7-11/h3-7,9,13-14,20-21H,8H2,1-2H3/t13?,14-/m0/s1
SMILES:	O=Cc1c2O[C@@H](CC(c2c(c(c1O)C)OC)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL301943
PubChem CID:	503269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	24.2	ug.mL-1	PMID[503676]

☑ 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 NPC471621 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	347
0.1-0.2	1509
0.2-0.3	3939
0.3-0.4	10350
0.4-0.5	8151
0.5-0.6	3804
0.6-0.7	5929
0.7-0.8	5506
0.8-0.85	1780
0.85-0.9	931
0.9-0.95	396
0.95-1	55

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC2416
0.9714	High Similarity	NPC476153
0.9714	High Similarity	NPC215885
0.971	High Similarity	NPC110038
0.971	High Similarity	NPC248372
0.9643	High Similarity	NPC271590
0.9643	High Similarity	NPC110776
0.964	High Similarity	NPC228504
0.964	High Similarity	NPC76372
0.964	High Similarity	NPC148757
0.964	High Similarity	NPC324436
0.964	High Similarity	NPC167624
0.964	High Similarity	NPC328164
0.964	High Similarity	NPC182852
0.964	High Similarity	NPC64915
0.964	High Similarity	NPC37496
0.964	High Similarity	NPC296917
0.964	High Similarity	NPC66515
0.964	High Similarity	NPC177354
0.964	High Similarity	NPC40833
0.964	High Similarity	NPC220998
0.964	High Similarity	NPC1089
0.964	High Similarity	NPC166934
0.964	High Similarity	NPC306829
0.964	High Similarity	NPC227579
0.964	High Similarity	NPC194432
0.964	High Similarity	NPC107572
0.964	High Similarity	NPC223500
0.964	High Similarity	NPC166482
0.964	High Similarity	NPC10937
0.964	High Similarity	NPC265040
0.964	High Similarity	NPC32739
0.964	High Similarity	NPC78
0.964	High Similarity	NPC76338
0.964	High Similarity	NPC324134
0.964	High Similarity	NPC125855
0.964	High Similarity	NPC161506
0.9574	High Similarity	NPC472629
0.9571	High Similarity	NPC68104
0.9571	High Similarity	NPC316816
0.9571	High Similarity	NPC81697
0.9571	High Similarity	NPC125894
0.9571	High Similarity	NPC75049
0.9571	High Similarity	NPC175504
0.9571	High Similarity	NPC257097
0.9571	High Similarity	NPC85162
0.9571	High Similarity	NPC150408
0.9571	High Similarity	NPC221432
0.9571	High Similarity	NPC143896
0.9571	High Similarity	NPC278249
0.9571	High Similarity	NPC91560
0.9571	High Similarity	NPC223812
0.9571	High Similarity	NPC478086
0.9571	High Similarity	NPC39329
0.9571	High Similarity	NPC149026
0.9571	High Similarity	NPC185276
0.9571	High Similarity	NPC214166
0.9571	High Similarity	NPC310130
0.9571	High Similarity	NPC107177
0.9571	High Similarity	NPC164980
0.9571	High Similarity	NPC169591
0.9571	High Similarity	NPC77794
0.9568	High Similarity	NPC258630
0.9568	High Similarity	NPC17170
0.9568	High Similarity	NPC96408
0.9568	High Similarity	NPC4743
0.9568	High Similarity	NPC156190
0.9568	High Similarity	NPC279650
0.9568	High Similarity	NPC312391
0.9568	High Similarity	NPC324386
0.9568	High Similarity	NPC213322
0.9568	High Similarity	NPC166689
0.951	High Similarity	NPC214493
0.9507	High Similarity	NPC472627
0.9504	High Similarity	NPC473015
0.9504	High Similarity	NPC124780
0.9504	High Similarity	NPC131579
0.9504	High Similarity	NPC473014
0.9504	High Similarity	NPC87486
0.9504	High Similarity	NPC235217
0.9504	High Similarity	NPC209040
0.9504	High Similarity	NPC236766
0.9504	High Similarity	NPC197252
0.9504	High Similarity	NPC131568
0.9504	High Similarity	NPC470890
0.9504	High Similarity	NPC473013
0.9496	High Similarity	NPC6407
0.9496	High Similarity	NPC110228
0.9496	High Similarity	NPC188243
0.9437	High Similarity	NPC214774
0.9437	High Similarity	NPC285630
0.9437	High Similarity	NPC470134
0.9437	High Similarity	NPC473078
0.9437	High Similarity	NPC176229
0.9437	High Similarity	NPC111786
0.9437	High Similarity	NPC67805
0.9437	High Similarity	NPC301276
0.9437	High Similarity	NPC470131
0.9437	High Similarity	NPC312973
0.9437	High Similarity	NPC195621
0.9437	High Similarity	NPC88964
0.9437	High Similarity	NPC475052
0.9437	High Similarity	NPC470647
0.9437	High Similarity	NPC127059
0.9437	High Similarity	NPC54577
0.9437	High Similarity	NPC109183
0.9437	High Similarity	NPC246948
0.9437	High Similarity	NPC470132
0.9437	High Similarity	NPC83357
0.9437	High Similarity	NPC142405
0.9437	High Similarity	NPC228779
0.9437	High Similarity	NPC267375
0.9437	High Similarity	NPC470133
0.9437	High Similarity	NPC20488
0.9429	High Similarity	NPC3188
0.9424	High Similarity	NPC310135
0.9424	High Similarity	NPC222342
0.9424	High Similarity	NPC53181
0.9424	High Similarity	NPC225153
0.9424	High Similarity	NPC20709
0.9424	High Similarity	NPC140890
0.9424	High Similarity	NPC217186
0.9424	High Similarity	NPC150648
0.9424	High Similarity	NPC265871
0.9424	High Similarity	NPC274784
0.9424	High Similarity	NPC329203
0.9375	High Similarity	NPC472628
0.9371	High Similarity	NPC473077
0.9371	High Similarity	NPC300988
0.9371	High Similarity	NPC23728
0.9371	High Similarity	NPC10990
0.9371	High Similarity	NPC296998
0.9371	High Similarity	NPC283234
0.9371	High Similarity	NPC110303
0.9366	High Similarity	NPC470136
0.9366	High Similarity	NPC271288
0.9366	High Similarity	NPC319752
0.9366	High Similarity	NPC224714
0.9366	High Similarity	NPC470135
0.9366	High Similarity	NPC39045
0.9362	High Similarity	NPC147145
0.9362	High Similarity	NPC266725
0.9357	High Similarity	NPC159275
0.9357	High Similarity	NPC129853
0.9357	High Similarity	NPC69769
0.9357	High Similarity	NPC284550
0.9357	High Similarity	NPC241100
0.9357	High Similarity	NPC76445
0.9353	High Similarity	NPC471620
0.931	High Similarity	NPC105136
0.9306	High Similarity	NPC161191
0.9306	High Similarity	NPC132592
0.9306	High Similarity	NPC160821
0.9301	High Similarity	NPC476088
0.9301	High Similarity	NPC187282
0.9301	High Similarity	NPC24136
0.9301	High Similarity	NPC290133
0.9301	High Similarity	NPC474161
0.9296	High Similarity	NPC106985
0.9296	High Similarity	NPC18585
0.9296	High Similarity	NPC166138
0.9291	High Similarity	NPC282300
0.9291	High Similarity	NPC110969
0.9291	High Similarity	NPC22467
0.9286	High Similarity	NPC18260
0.9286	High Similarity	NPC55018
0.9286	High Similarity	NPC301217
0.9286	High Similarity	NPC303633
0.9286	High Similarity	NPC220062
0.9286	High Similarity	NPC96565
0.9286	High Similarity	NPC216978
0.9286	High Similarity	NPC139554
0.9286	High Similarity	NPC78913
0.9286	High Similarity	NPC470211
0.9281	High Similarity	NPC12296
0.9281	High Similarity	NPC296490
0.9281	High Similarity	NPC79943
0.9281	High Similarity	NPC295261
0.9281	High Similarity	NPC259685
0.9281	High Similarity	NPC287246
0.9281	High Similarity	NPC107586
0.9281	High Similarity	NPC243083
0.9281	High Similarity	NPC13768
0.9281	High Similarity	NPC32441
0.9252	High Similarity	NPC122365
0.9247	High Similarity	NPC262039
0.9247	High Similarity	NPC262038
0.9247	High Similarity	NPC319910
0.9247	High Similarity	NPC472422
0.9247	High Similarity	NPC471676
0.9247	High Similarity	NPC254412
0.9247	High Similarity	NPC471677
0.9247	High Similarity	NPC263384
0.9247	High Similarity	NPC278476
0.9247	High Similarity	NPC472420
0.9247	High Similarity	NPC244577
0.9241	High Similarity	NPC5173
0.9241	High Similarity	NPC3642
0.9241	High Similarity	NPC473016
0.9241	High Similarity	NPC19238

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 NPC471621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	934
0.2-0.3	1549
0.3-0.4	2654
0.4-0.5	1898
0.5-0.6	1181
0.6-0.7	432
0.7-0.8	142
0.8-0.85	26
0.85-0.9	16
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD1550	Clinical (unspecified phase)
0.9281	High Similarity	NPD1552	Clinical (unspecified phase)
0.9214	High Similarity	NPD1549	Phase 2
0.9097	High Similarity	NPD4378	Clinical (unspecified phase)
0.8993	High Similarity	NPD2393	Clinical (unspecified phase)
0.8966	High Similarity	NPD7410	Clinical (unspecified phase)
0.8933	High Similarity	NPD8443	Clinical (unspecified phase)
0.8919	High Similarity	NPD4380	Phase 2
0.8859	High Similarity	NPD7411	Suspended
0.8816	High Similarity	NPD7075	Discontinued
0.8803	High Similarity	NPD2796	Approved
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8732	High Similarity	NPD1510	Phase 2
0.8714	High Similarity	NPD1240	Approved
0.8675	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD6801	Discontinued
0.8618	High Similarity	NPD7819	Suspended
0.8592	High Similarity	NPD1607	Approved
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1551	Phase 2
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8389	Intermediate Similarity	NPD6799	Approved
0.8387	Intermediate Similarity	NPD7768	Phase 2
0.8367	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6166	Phase 2
0.8365	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6559	Discontinued
0.8267	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD2801	Approved
0.8243	Intermediate Similarity	NPD2800	Approved
0.8207	Intermediate Similarity	NPD6651	Approved
0.8182	Intermediate Similarity	NPD6599	Discontinued
0.816	Intermediate Similarity	NPD7074	Phase 3
0.8158	Intermediate Similarity	NPD1512	Approved
0.8153	Intermediate Similarity	NPD3882	Suspended
0.8113	Intermediate Similarity	NPD5494	Approved
0.8105	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD920	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD2534	Approved
0.8092	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD2532	Approved
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3750	Approved
0.8056	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7472	Approved
0.8041	Intermediate Similarity	NPD2935	Discontinued
0.8038	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8014	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5124	Phase 1
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD5401	Approved
0.7973	Intermediate Similarity	NPD7033	Discontinued
0.7952	Intermediate Similarity	NPD7251	Discontinued
0.7947	Intermediate Similarity	NPD4628	Phase 3
0.7929	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4908	Phase 1
0.7904	Intermediate Similarity	NPD7808	Phase 3
0.7901	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD5953	Discontinued
0.7881	Intermediate Similarity	NPD1243	Approved
0.7879	Intermediate Similarity	NPD7286	Phase 2
0.7852	Intermediate Similarity	NPD2799	Discontinued
0.7832	Intermediate Similarity	NPD1203	Approved
0.7829	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD2313	Discontinued
0.7801	Intermediate Similarity	NPD1610	Phase 2
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6832	Phase 2
0.7785	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1548	Phase 1
0.7759	Intermediate Similarity	NPD4360	Phase 2
0.7759	Intermediate Similarity	NPD4363	Phase 3
0.7758	Intermediate Similarity	NPD7473	Discontinued
0.775	Intermediate Similarity	NPD5402	Approved
0.7748	Intermediate Similarity	NPD2344	Approved
0.7733	Intermediate Similarity	NPD3748	Approved
0.7716	Intermediate Similarity	NPD919	Approved
0.7682	Intermediate Similarity	NPD6100	Approved
0.7682	Intermediate Similarity	NPD6099	Approved
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD9717	Approved
0.7622	Intermediate Similarity	NPD1247	Approved
0.7616	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2797	Approved
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
0.7574	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3268	Approved
0.7552	Intermediate Similarity	NPD422	Phase 1
0.7548	Intermediate Similarity	NPD2309	Approved
0.7547	Intermediate Similarity	NPD3226	Approved
0.7547	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7467	Intermediate Similarity	NPD943	Approved
0.7452	Intermediate Similarity	NPD7390	Discontinued
0.745	Intermediate Similarity	NPD6798	Discontinued
0.7419	Intermediate Similarity	NPD2654	Approved
0.7417	Intermediate Similarity	NPD1933	Approved
0.7415	Intermediate Similarity	NPD2798	Approved
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7403	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3225	Approved
0.7394	Intermediate Similarity	NPD9545	Approved
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7362	Intermediate Similarity	NPD1465	Phase 2
0.7362	Intermediate Similarity	NPD5760	Phase 2
0.7362	Intermediate Similarity	NPD5761	Phase 2
0.7346	Intermediate Similarity	NPD5890	Approved
0.7346	Intermediate Similarity	NPD5889	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3926	Phase 2
0.7315	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1652	Phase 2
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7584	Approved
0.729	Intermediate Similarity	NPD6004	Phase 3
0.729	Intermediate Similarity	NPD6005	Phase 3
0.729	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6002	Phase 3
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.726	Intermediate Similarity	NPD1608	Approved
0.726	Intermediate Similarity	NPD3972	Approved
0.7256	Intermediate Similarity	NPD8455	Phase 2
0.7254	Intermediate Similarity	NPD9493	Approved
0.7253	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2861	Phase 2
0.7244	Intermediate Similarity	NPD2424	Discontinued
0.7241	Intermediate Similarity	NPD8312	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7233	Intermediate Similarity	NPD7212	Phase 2
0.7233	Intermediate Similarity	NPD7213	Phase 3
0.723	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD3267	Approved
0.7226	Intermediate Similarity	NPD5405	Approved
0.7226	Intermediate Similarity	NPD5404	Approved
0.7226	Intermediate Similarity	NPD5406	Approved
0.7226	Intermediate Similarity	NPD5408	Approved
0.7225	Intermediate Similarity	NPD6104	Discontinued
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7219	Intermediate Similarity	NPD1296	Phase 2
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7212	Intermediate Similarity	NPD4288	Approved
0.7211	Intermediate Similarity	NPD4749	Approved
0.7205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.7195	Intermediate Similarity	NPD6844	Discontinued
0.7193	Intermediate Similarity	NPD3751	Discontinued
0.719	Intermediate Similarity	NPD230	Phase 1
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD4662	Approved
0.7188	Intermediate Similarity	NPD4661	Approved
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7178	Intermediate Similarity	NPD6585	Discontinued
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7153	Intermediate Similarity	NPD1894	Discontinued
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD4287	Approved
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4307	Phase 2
0.7115	Intermediate Similarity	NPD4477	Approved
0.7115	Intermediate Similarity	NPD4476	Approved
0.7114	Intermediate Similarity	NPD1164	Approved
0.7105	Intermediate Similarity	NPD411	Approved
0.7105	Intermediate Similarity	NPD3764	Approved
0.7093	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD37	Approved
0.7089	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7447	Phase 1
0.7081	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD447	Suspended
0.7076	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1201	Approved
0.7069	Intermediate Similarity	NPD3823	Discontinued
0.7066	Intermediate Similarity	NPD4965	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