NPASS Compound

Structure

NPC157497 OpenBabel07101719522D 36 38 0 0 1 0 0 0 0 0999 V2000 1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0629 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 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 10 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 6 27 2 0 0 0 0 7 14 1 0 0 0 0 7 28 2 0 0 0 0 8 15 1 0 0 0 0 8 29 2 0 0 0 0 9 16 1 0 0 0 0 9 30 2 0 0 0 0 12 5 1 6 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 2 0 0 0 0 13 23 1 0 0 0 0 14 20 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 21 1 0 0 0 0 16 25 2 0 0 0 0 17 11 1 1 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 19 1 6 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.17
Volume:	494.12
LogP:	6.183
LogD:	1.815
LogS:	-2.745
# Rotatable Bonds:	8
TPSA:	178.66
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	4.682
Fsp3:	0.385
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.676
MDCK Permeability:	3.325611942273099e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.306
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	101.55972290039062%
Volume Distribution (VD):	0.634
Pgp-substrate:	1.6828747987747192%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.637
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	0.048
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.643
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.91
Respiratory Toxicity:	0.378

Download Data

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

Natural Product: NPC157497

Natural Product ID:	NPC157497
*Common Name:**	Sideroxylonal C
IUPAC Name:	(2R,3R,4R)-2-(3,5-diformyl-2,4,6-trihydroxyphenyl)-5,7-dihydroxy-4-(2-methylpropyl)-3-propan-2-yl-3,4-dihydro-2H-chromene-6,8-dicarbaldehyde
Synonyms:	Sideroxylonal C
Standard InCHIKey:	PHQDMQGEKNBIPF-RAFFTOIBSA-N
Standard InCHI:	InChI=1S/C26H28O10/c1-10(2)5-12-17(11(3)4)26(19-23(34)13(6-27)20(31)14(7-28)24(19)35)36-25-16(9-30)21(32)15(8-29)22(33)18(12)25/h6-12,17,26,31-35H,5H2,1-4H3/t12-,17-,26-/m1/s1
SMILES:	CC(C)C[C@@H]1[C@@H](C(C)C)[C@H](c2c(c(C=O)c(c(C=O)c2O)O)O)Oc2c(C=O)c(c(C=O)c(c12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453538
PubChem CID:	10413640
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002993] 7-hydroxyflavonoids

*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
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO19242	Eucalyptus albens	Species	Myrtaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3953	Individual Protein	Plasminogen activator inhibitor-1	Homo sapiens	IC50	=	4700.0	nM	PMID[461155]

☑ 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 NPC157497 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	364
0.1-0.2	1610
0.2-0.3	3896
0.3-0.4	10319
0.4-0.5	9087
0.5-0.6	4202
0.6-0.7	6221
0.7-0.8	5169
0.8-0.85	1257
0.85-0.9	540
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC81337
1.0	High Similarity	NPC285659
0.9291	High Similarity	NPC5990
0.9231	High Similarity	NPC304351
0.9231	High Similarity	NPC245757
0.9161	High Similarity	NPC82534
0.9161	High Similarity	NPC476153
0.9161	High Similarity	NPC2416
0.9161	High Similarity	NPC215885
0.9155	High Similarity	NPC112749
0.9155	High Similarity	NPC471621
0.9103	High Similarity	NPC214493
0.9091	High Similarity	NPC110776
0.9091	High Similarity	NPC271288
0.9091	High Similarity	NPC271590
0.9021	High Similarity	NPC278249
0.9021	High Similarity	NPC77794
0.9021	High Similarity	NPC125894
0.9021	High Similarity	NPC223812
0.9021	High Similarity	NPC81697
0.9021	High Similarity	NPC107177
0.9021	High Similarity	NPC85162
0.9014	High Similarity	NPC279650
0.9014	High Similarity	NPC110038
0.9014	High Similarity	NPC258630
0.9014	High Similarity	NPC17170
0.9014	High Similarity	NPC96408
0.9014	High Similarity	NPC156190
0.9014	High Similarity	NPC248372
0.9014	High Similarity	NPC166689
0.9007	High Similarity	NPC240305
0.8973	High Similarity	NPC473016
0.8971	High Similarity	NPC186628
0.8966	High Similarity	NPC308200
0.8966	High Similarity	NPC10990
0.8966	High Similarity	NPC300988
0.8958	High Similarity	NPC235217
0.8958	High Similarity	NPC470890
0.8958	High Similarity	NPC473015
0.8958	High Similarity	NPC131568
0.8958	High Similarity	NPC473014
0.8958	High Similarity	NPC131579
0.8958	High Similarity	NPC473013
0.8951	High Similarity	NPC223500
0.8951	High Similarity	NPC66515
0.8951	High Similarity	NPC1089
0.8951	High Similarity	NPC76338
0.8951	High Similarity	NPC220998
0.8951	High Similarity	NPC328164
0.8951	High Similarity	NPC182852
0.8951	High Similarity	NPC10937
0.8951	High Similarity	NPC64915
0.8951	High Similarity	NPC32739
0.8951	High Similarity	NPC227579
0.8951	High Similarity	NPC148757
0.8951	High Similarity	NPC265040
0.8951	High Similarity	NPC37496
0.8951	High Similarity	NPC40833
0.8951	High Similarity	NPC76372
0.8951	High Similarity	NPC324134
0.8951	High Similarity	NPC306829
0.8951	High Similarity	NPC161506
0.8951	High Similarity	NPC296917
0.8951	High Similarity	NPC228504
0.8951	High Similarity	NPC125855
0.8951	High Similarity	NPC78
0.8951	High Similarity	NPC166934
0.8951	High Similarity	NPC166482
0.8951	High Similarity	NPC107572
0.8951	High Similarity	NPC167624
0.8951	High Similarity	NPC194432
0.8951	High Similarity	NPC324436
0.8951	High Similarity	NPC177354
0.8944	High Similarity	NPC469818
0.8936	High Similarity	NPC272844
0.8936	High Similarity	NPC254168
0.8936	High Similarity	NPC248995
0.8905	High Similarity	NPC279566
0.8904	High Similarity	NPC145467
0.8904	High Similarity	NPC39195
0.8897	High Similarity	NPC285630
0.8897	High Similarity	NPC187282
0.8897	High Similarity	NPC290133
0.8897	High Similarity	NPC24136
0.8897	High Similarity	NPC73320
0.8897	High Similarity	NPC477955
0.8897	High Similarity	NPC127059
0.8897	High Similarity	NPC472629
0.8897	High Similarity	NPC228779
0.8889	High Similarity	NPC91560
0.8889	High Similarity	NPC478086
0.8889	High Similarity	NPC185276
0.8889	High Similarity	NPC164980
0.8889	High Similarity	NPC75049
0.8889	High Similarity	NPC175504
0.8889	High Similarity	NPC316816
0.8889	High Similarity	NPC310130
0.8889	High Similarity	NPC221432
0.8889	High Similarity	NPC169591
0.8889	High Similarity	NPC68104
0.8889	High Similarity	NPC149026
0.8889	High Similarity	NPC214166
0.8889	High Similarity	NPC150408
0.8889	High Similarity	NPC39329
0.8889	High Similarity	NPC143896
0.8889	High Similarity	NPC257097
0.8881	High Similarity	NPC476508
0.8881	High Similarity	NPC312391
0.8881	High Similarity	NPC4743
0.8881	High Similarity	NPC213322
0.8881	High Similarity	NPC324386
0.8873	High Similarity	NPC140890
0.8865	High Similarity	NPC255801
0.8865	High Similarity	NPC322301
0.8851	High Similarity	NPC209142
0.8851	High Similarity	NPC178484
0.8851	High Similarity	NPC312549
0.8844	High Similarity	NPC471114
0.8836	High Similarity	NPC474108
0.8836	High Similarity	NPC473077
0.8836	High Similarity	NPC177995
0.8836	High Similarity	NPC296998
0.8828	High Similarity	NPC311144
0.8828	High Similarity	NPC87486
0.8828	High Similarity	NPC224714
0.8828	High Similarity	NPC197252
0.8828	High Similarity	NPC236766
0.8828	High Similarity	NPC124780
0.8828	High Similarity	NPC209040
0.8819	High Similarity	NPC202981
0.8811	High Similarity	NPC110228
0.8811	High Similarity	NPC129853
0.8811	High Similarity	NPC188243
0.8811	High Similarity	NPC284550
0.8811	High Similarity	NPC6407
0.8811	High Similarity	NPC76445
0.8794	High Similarity	NPC470983
0.8794	High Similarity	NPC470982
0.8792	High Similarity	NPC475131
0.8792	High Similarity	NPC473770
0.8792	High Similarity	NPC473509
0.8792	High Similarity	NPC87708
0.8784	High Similarity	NPC471115
0.8784	High Similarity	NPC29777
0.8784	High Similarity	NPC476509
0.8777	High Similarity	NPC215875
0.8777	High Similarity	NPC15834
0.8776	High Similarity	NPC472345
0.8767	High Similarity	NPC470132
0.8767	High Similarity	NPC470131
0.8767	High Similarity	NPC67805
0.8767	High Similarity	NPC470647
0.8767	High Similarity	NPC246948
0.8767	High Similarity	NPC142405
0.8767	High Similarity	NPC176229
0.8767	High Similarity	NPC474161
0.8767	High Similarity	NPC470134
0.8767	High Similarity	NPC54577
0.8767	High Similarity	NPC301276
0.8767	High Similarity	NPC195621
0.8767	High Similarity	NPC473078
0.8767	High Similarity	NPC88964
0.8767	High Similarity	NPC20488
0.8767	High Similarity	NPC109183
0.8767	High Similarity	NPC111786
0.8767	High Similarity	NPC476088
0.8767	High Similarity	NPC299011
0.8767	High Similarity	NPC214774
0.8767	High Similarity	NPC312973
0.8767	High Similarity	NPC470133
0.8767	High Similarity	NPC267375
0.8767	High Similarity	NPC83357
0.8767	High Similarity	NPC475052
0.8759	High Similarity	NPC18886
0.8759	High Similarity	NPC106985
0.8759	High Similarity	NPC262935
0.8759	High Similarity	NPC18585
0.8759	High Similarity	NPC172182
0.8759	High Similarity	NPC251182
0.8759	High Similarity	NPC113770
0.8759	High Similarity	NPC166138
0.875	High Similarity	NPC3188
0.875	High Similarity	NPC22467
0.875	High Similarity	NPC282300
0.8741	High Similarity	NPC310135
0.8741	High Similarity	NPC274784
0.8741	High Similarity	NPC53181
0.8741	High Similarity	NPC329203
0.8741	High Similarity	NPC265871
0.8741	High Similarity	NPC20709
0.8741	High Similarity	NPC222342
0.8741	High Similarity	NPC150648
0.8741	High Similarity	NPC316480
0.8741	High Similarity	NPC225153
0.8741	High Similarity	NPC217186
0.8733	High Similarity	NPC122365
0.8725	High Similarity	NPC232645
0.8725	High Similarity	NPC72958
0.8725	High Similarity	NPC148945
0.8725	High Similarity	NPC473131

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 NPC157497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	1035
0.2-0.3	1978
0.3-0.4	2679
0.4-0.5	1768
0.5-0.6	961
0.6-0.7	290
0.7-0.8	92
0.8-0.85	22
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD8443	Clinical (unspecified phase)
0.8601	High Similarity	NPD1550	Clinical (unspecified phase)
0.8601	High Similarity	NPD1552	Clinical (unspecified phase)
0.8582	High Similarity	NPD6651	Approved
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8542	High Similarity	NPD1549	Phase 2
0.8487	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD7411	Suspended
0.8446	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7075	Discontinued
0.8411	Intermediate Similarity	NPD4380	Phase 2
0.8397	Intermediate Similarity	NPD6959	Discontinued
0.8366	Intermediate Similarity	NPD7819	Suspended
0.8356	Intermediate Similarity	NPD2800	Approved
0.8276	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1510	Phase 2
0.8182	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8089	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2533	Approved
0.8079	Intermediate Similarity	NPD2532	Approved
0.8056	Intermediate Similarity	NPD1240	Approved
0.8025	Intermediate Similarity	NPD7768	Phase 2
0.7975	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1607	Approved
0.7919	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1551	Phase 2
0.7901	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6166	Phase 2
0.7875	Intermediate Similarity	NPD5494	Approved
0.7867	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6559	Discontinued
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2801	Approved
0.7778	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD1511	Approved
0.7742	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD7074	Phase 3
0.7707	Intermediate Similarity	NPD6599	Discontinued
0.7697	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD3882	Suspended
0.7679	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1512	Approved
0.7671	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6232	Discontinued
0.7655	Intermediate Similarity	NPD4908	Phase 1
0.7651	Intermediate Similarity	NPD7054	Approved
0.764	Intermediate Similarity	NPD3749	Approved
0.7636	Intermediate Similarity	NPD7473	Discontinued
0.7635	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD5124	Phase 1
0.7625	Intermediate Similarity	NPD3817	Phase 2
0.7605	Intermediate Similarity	NPD7472	Approved
0.76	Intermediate Similarity	NPD2799	Discontinued
0.7597	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3818	Discontinued
0.7561	Intermediate Similarity	NPD5711	Approved
0.7561	Intermediate Similarity	NPD5710	Approved
0.756	Intermediate Similarity	NPD6797	Phase 2
0.756	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.755	Intermediate Similarity	NPD2935	Discontinued
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7535	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD5403	Approved
0.7515	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4360	Phase 2
0.7443	Intermediate Similarity	NPD4363	Phase 3
0.744	Intermediate Similarity	NPD7286	Phase 2
0.7421	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD5401	Approved
0.7386	Intermediate Similarity	NPD2344	Approved
0.7368	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7390	Discontinued
0.7315	Intermediate Similarity	NPD2313	Discontinued
0.7315	Intermediate Similarity	NPD3268	Approved
0.7301	Intermediate Similarity	NPD5402	Approved
0.7297	Intermediate Similarity	NPD6832	Phase 2
0.7292	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD919	Approved
0.7255	Intermediate Similarity	NPD7033	Discontinued
0.7251	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2797	Approved
0.7211	Intermediate Similarity	NPD1203	Approved
0.7207	Intermediate Similarity	NPD4361	Phase 2
0.7207	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2309	Approved
0.7169	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2798	Approved
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD3926	Phase 2
0.7086	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4749	Approved
0.7072	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7229	Phase 3
0.7039	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5760	Phase 2
0.703	Intermediate Similarity	NPD5761	Phase 2
0.7029	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8312	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD2861	Phase 2
0.6994	Remote Similarity	NPD1729	Discontinued
0.6994	Remote Similarity	NPD7458	Discontinued
0.6993	Remote Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD943	Approved
0.6993	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7199	Phase 2
0.698	Remote Similarity	NPD3266	Approved
0.698	Remote Similarity	NPD3267	Approved
0.697	Remote Similarity	NPD37	Approved
0.6964	Remote Similarity	NPD6234	Discontinued
0.6962	Remote Similarity	NPD2654	Approved
0.6959	Remote Similarity	NPD2403	Approved
0.6948	Remote Similarity	NPD6355	Discontinued
0.6946	Remote Similarity	NPD4965	Approved
0.6946	Remote Similarity	NPD4967	Phase 2
0.6946	Remote Similarity	NPD4966	Approved
0.6943	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6004	Phase 3
0.6943	Remote Similarity	NPD6005	Phase 3
0.6943	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD422	Phase 1
0.6928	Remote Similarity	NPD8455	Phase 2
0.6923	Remote Similarity	NPD4308	Phase 3
0.6918	Remote Similarity	NPD7003	Approved
0.6915	Remote Similarity	NPD7584	Approved
0.6913	Remote Similarity	NPD3225	Approved
0.6909	Remote Similarity	NPD5889	Approved
0.6909	Remote Similarity	NPD5890	Approved
0.6901	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4288	Approved
0.6879	Remote Similarity	NPD5404	Approved
0.6879	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD5408	Approved
0.6879	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5405	Approved
0.6871	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6798	Discontinued
0.6842	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD230	Phase 1
0.6839	Remote Similarity	NPD1933	Approved
0.6839	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4287	Approved
0.6818	Remote Similarity	NPD6104	Discontinued
0.681	Remote Similarity	NPD6273	Approved
0.6803	Remote Similarity	NPD17	Approved
0.6782	Remote Similarity	NPD7228	Approved
0.6782	Remote Similarity	NPD3751	Discontinued
0.6781	Remote Similarity	NPD9545	Approved
0.6779	Remote Similarity	NPD3972	Approved
0.6774	Remote Similarity	NPD6782	Approved
0.6774	Remote Similarity	NPD4060	Phase 1
0.6774	Remote Similarity	NPD6777	Approved
0.6774	Remote Similarity	NPD6779	Approved
0.6774	Remote Similarity	NPD6778	Approved
0.6774	Remote Similarity	NPD6776	Approved
0.6774	Remote Similarity	NPD6781	Approved
0.6774	Remote Similarity	NPD6780	Approved
0.6772	Remote Similarity	NPD4477	Approved
0.6772	Remote Similarity	NPD4476	Approved
0.6755	Remote Similarity	NPD1164	Approved
0.6754	Remote Similarity	NPD8151	Discontinued
0.6753	Remote Similarity	NPD3764	Approved
0.6747	Remote Similarity	NPD6585	Discontinued
0.6744	Remote Similarity	NPD3787	Discontinued
0.674	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1471	Phase 3
0.6722	Remote Similarity	NPD8150	Discontinued
0.6711	Remote Similarity	NPD1201	Approved
0.6688	Remote Similarity	NPD3027	Phase 3

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