NPASS Compound

Structure

NPC476301 OpenBabel07101719522D 38 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4128 0.0296 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6915 -2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -4.3005 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 -2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -1.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9128 -4.3005 0.0000 C 0 0 1 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 6.9128 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4128 -3.4345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9128 -0.8364 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 2.7405 -1.8546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -5.1665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4128 -5.1665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4128 -3.4345 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4128 0.0296 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 17 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 27 1 0 0 0 0 10 16 1 0 0 0 0 10 28 1 0 0 0 0 11 1 1 1 0 0 0 11 20 1 0 0 0 0 11 36 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 2 0 0 0 0 15 9 1 6 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 29 1 1 0 0 0 17 18 2 0 0 0 0 17 37 1 0 0 0 0 18 34 1 0 0 0 0 19 25 1 0 0 0 0 19 35 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 6 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 12 1 1 0 0 0 24 38 1 0 0 0 0 25 38 1 0 0 0 0 26 36 1 0 0 0 0 26 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.21
Volume:	513.69
LogP:	-0.2
LogD:	-0.302
LogS:	-3.794
# Rotatable Bonds:	9
TPSA:	187.76
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	4.601
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.334
MDCK Permeability:	6.241686060093343e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.455
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	48.96794509887695%
Volume Distribution (VD):	0.385
Pgp-substrate:	25.038707733154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.337
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	1.871
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.232
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.636
AMES Toxicity:	0.144
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.35
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC476301

Natural Product ID:	NPC476301
*Common Name:**	4-O-Rhamnosyl-7S,8R-7',8'-Erythro-Sismbrifolin
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-[(1R,2S)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	NQHFIYPUIVKCLI-KNJWWJHHSA-N
Standard InCHI:	InChI=1S/C26H34O12/c1-11-20(30)22(32)23(33)26(36-11)37-17-5-4-12(7-18(17)34-2)24-15(9-27)14-6-13(21(31)16(29)10-28)8-19(35-3)25(14)38-24/h4-8,11,15-16,20-24,26-33H,9-10H2,1-3H3/t11-,15-,16-,20-,21+,22+,23+,24+,26-/m0/s1
SMILES:	OC[C@@H]([C@@H](c1cc2[C@H](CO)[C@H](Oc2c(c1)OC)c1ccc(c(c1)OC)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562877
PubChem CID:	45272229
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran 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
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361168]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	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
EC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Ratio	=	1.84	n.a.	PMID[473779]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	9070.0	nM	PMID[473779]

☑ 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 NPC476301 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	414
0.1-0.2	1455
0.2-0.3	3594
0.3-0.4	9150
0.4-0.5	9343
0.5-0.6	4804
0.6-0.7	8298
0.7-0.8	4448
0.8-0.85	799
0.85-0.9	330
0.9-0.95	44
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43508
0.9927	High Similarity	NPC217635
0.9927	High Similarity	NPC79429
0.9927	High Similarity	NPC471667
0.9856	High Similarity	NPC213074
0.9856	High Similarity	NPC275284
0.9856	High Similarity	NPC193473
0.9856	High Similarity	NPC224674
0.9856	High Similarity	NPC15956
0.9856	High Similarity	NPC114505
0.9856	High Similarity	NPC31325
0.9648	High Similarity	NPC98624
0.9645	High Similarity	NPC270751
0.9568	High Similarity	NPC470950
0.9568	High Similarity	NPC185307
0.951	High Similarity	NPC472709
0.951	High Similarity	NPC472710
0.95	High Similarity	NPC283995
0.95	High Similarity	NPC470235
0.95	High Similarity	NPC129417
0.9496	High Similarity	NPC246947
0.9496	High Similarity	NPC253878
0.9496	High Similarity	NPC476356
0.9433	High Similarity	NPC22150
0.9433	High Similarity	NPC38041
0.9433	High Similarity	NPC279298
0.9429	High Similarity	NPC46092
0.9424	High Similarity	NPC471414
0.9424	High Similarity	NPC472711
0.9379	High Similarity	NPC302610
0.9366	High Similarity	NPC112861
0.9362	High Similarity	NPC471063
0.9301	High Similarity	NPC39657
0.9296	High Similarity	NPC18979
0.9291	High Similarity	NPC477898
0.9281	High Similarity	NPC156376
0.927	High Similarity	NPC476411
0.927	High Similarity	NPC187194
0.9257	High Similarity	NPC228357
0.9247	High Similarity	NPC474442
0.9231	High Similarity	NPC205796
0.9231	High Similarity	NPC276753
0.9225	High Similarity	NPC84181
0.922	High Similarity	NPC302506
0.9209	High Similarity	NPC138738
0.9209	High Similarity	NPC470413
0.9197	High Similarity	NPC26394
0.9172	High Similarity	NPC286235
0.9172	High Similarity	NPC44452
0.9172	High Similarity	NPC51328
0.9172	High Similarity	NPC55158
0.9161	High Similarity	NPC475096
0.9149	High Similarity	NPC471908
0.9137	High Similarity	NPC209985
0.9137	High Similarity	NPC263367
0.9137	High Similarity	NPC29799
0.9137	High Similarity	NPC199459
0.9137	High Similarity	NPC52277
0.9137	High Similarity	NPC156502
0.9137	High Similarity	NPC54743
0.9137	High Similarity	NPC477939
0.9137	High Similarity	NPC10737
0.9137	High Similarity	NPC177160
0.9137	High Similarity	NPC177035
0.9133	High Similarity	NPC478269
0.9124	High Similarity	NPC230219
0.911	High Similarity	NPC475224
0.9103	High Similarity	NPC130449
0.9103	High Similarity	NPC248132
0.9097	High Similarity	NPC99515
0.9097	High Similarity	NPC190714
0.9091	High Similarity	NPC472712
0.9091	High Similarity	NPC179521
0.9091	High Similarity	NPC164183
0.9091	High Similarity	NPC473046
0.9091	High Similarity	NPC118385
0.9091	High Similarity	NPC187774
0.9091	High Similarity	NPC472713
0.9085	High Similarity	NPC60249
0.9078	High Similarity	NPC106944
0.9065	High Similarity	NPC79957
0.9065	High Similarity	NPC101624
0.9065	High Similarity	NPC184938
0.9058	High Similarity	NPC25821
0.9034	High Similarity	NPC227902
0.9028	High Similarity	NPC272619
0.9028	High Similarity	NPC469586
0.9028	High Similarity	NPC286245
0.9028	High Similarity	NPC180953
0.9028	High Similarity	NPC181615
0.9021	High Similarity	NPC278961
0.9021	High Similarity	NPC113680
0.9014	High Similarity	NPC76871
0.9013	High Similarity	NPC478267
0.9007	High Similarity	NPC241600
0.9007	High Similarity	NPC173726
0.8993	High Similarity	NPC193026
0.8993	High Similarity	NPC90083
0.8993	High Similarity	NPC170779
0.8993	High Similarity	NPC49603
0.8993	High Similarity	NPC187616
0.8986	High Similarity	NPC18842
0.898	High Similarity	NPC229882
0.898	High Similarity	NPC183380
0.898	High Similarity	NPC158635
0.898	High Similarity	NPC238140
0.8978	High Similarity	NPC80600
0.8978	High Similarity	NPC472024
0.8973	High Similarity	NPC175976
0.8973	High Similarity	NPC71726
0.8966	High Similarity	NPC241846
0.8966	High Similarity	NPC260397
0.8966	High Similarity	NPC93610
0.8966	High Similarity	NPC125755
0.8958	High Similarity	NPC473045
0.8958	High Similarity	NPC25292
0.8958	High Similarity	NPC253015
0.8958	High Similarity	NPC471065
0.8951	High Similarity	NPC131971
0.8951	High Similarity	NPC189115
0.8951	High Similarity	NPC469559
0.8951	High Similarity	NPC5262
0.8951	High Similarity	NPC475084
0.8951	High Similarity	NPC472714
0.8936	High Similarity	NPC304152
0.8936	High Similarity	NPC477938
0.8929	High Similarity	NPC93783
0.8926	High Similarity	NPC115466
0.8926	High Similarity	NPC245615
0.8926	High Similarity	NPC61604
0.8926	High Similarity	NPC299706
0.8913	High Similarity	NPC9912
0.8912	High Similarity	NPC35877
0.8912	High Similarity	NPC240521
0.8912	High Similarity	NPC95392
0.8912	High Similarity	NPC55715
0.8905	High Similarity	NPC26653
0.8905	High Similarity	NPC248355
0.8905	High Similarity	NPC270849
0.8905	High Similarity	NPC166040
0.8904	High Similarity	NPC99183
0.8897	High Similarity	NPC161700
0.8897	High Similarity	NPC307466
0.8897	High Similarity	NPC277867
0.8889	High Similarity	NPC473044
0.8889	High Similarity	NPC81638
0.8881	High Similarity	NPC263261
0.8881	High Similarity	NPC87725
0.8881	High Similarity	NPC108674
0.8881	High Similarity	NPC469661
0.8873	High Similarity	NPC292487
0.8867	High Similarity	NPC159922
0.8865	High Similarity	NPC77861
0.8865	High Similarity	NPC172818
0.8865	High Similarity	NPC25695
0.8859	High Similarity	NPC59692
0.8859	High Similarity	NPC21902
0.8857	High Similarity	NPC35731
0.8857	High Similarity	NPC470881
0.8857	High Similarity	NPC16485
0.8857	High Similarity	NPC478085
0.8851	High Similarity	NPC469707
0.8851	High Similarity	NPC185955
0.8851	High Similarity	NPC225815
0.8851	High Similarity	NPC469706
0.8851	High Similarity	NPC218041
0.8851	High Similarity	NPC214326
0.8851	High Similarity	NPC260781
0.8851	High Similarity	NPC9933
0.8851	High Similarity	NPC182368
0.8851	High Similarity	NPC145979
0.8849	High Similarity	NPC259742
0.8849	High Similarity	NPC104077
0.8849	High Similarity	NPC219671
0.8849	High Similarity	NPC147616
0.8849	High Similarity	NPC471505
0.8849	High Similarity	NPC106739
0.8844	High Similarity	NPC159697
0.8844	High Similarity	NPC304048
0.8844	High Similarity	NPC303013
0.8844	High Similarity	NPC301961
0.8844	High Similarity	NPC166584
0.8844	High Similarity	NPC130959
0.8844	High Similarity	NPC474795
0.8844	High Similarity	NPC226153
0.8844	High Similarity	NPC474940
0.8836	High Similarity	NPC162193
0.8832	High Similarity	NPC470084
0.8832	High Similarity	NPC302378
0.8828	High Similarity	NPC76176
0.8828	High Similarity	NPC168579
0.8828	High Similarity	NPC12641
0.8828	High Similarity	NPC63879
0.8828	High Similarity	NPC280092
0.8828	High Similarity	NPC469313
0.8828	High Similarity	NPC93323
0.8828	High Similarity	NPC133251
0.8828	High Similarity	NPC45257
0.8828	High Similarity	NPC138227
0.8819	High Similarity	NPC41782

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 NPC476301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	805
0.2-0.3	1700
0.3-0.4	2778
0.4-0.5	1782
0.5-0.6	1010
0.6-0.7	617
0.7-0.8	113
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD6674	Discontinued
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1613	Approved
0.8194	Intermediate Similarity	NPD37	Approved
0.8188	Intermediate Similarity	NPD1091	Approved
0.8153	Intermediate Similarity	NPD4965	Approved
0.8153	Intermediate Similarity	NPD4967	Phase 2
0.8153	Intermediate Similarity	NPD4966	Approved
0.8148	Intermediate Similarity	NPD7228	Approved
0.8112	Intermediate Similarity	NPD3027	Phase 3
0.8108	Intermediate Similarity	NPD7266	Discontinued
0.8099	Intermediate Similarity	NPD2861	Phase 2
0.8079	Intermediate Similarity	NPD5058	Phase 3
0.8063	Intermediate Similarity	NPD7199	Phase 2
0.8058	Intermediate Similarity	NPD3705	Approved
0.8052	Intermediate Similarity	NPD1653	Approved
0.805	Intermediate Similarity	NPD6234	Discontinued
0.8042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8455	Phase 2
0.8	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7931	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7879	Intermediate Similarity	NPD7054	Approved
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7240	Approved
0.7842	Intermediate Similarity	NPD1357	Approved
0.7831	Intermediate Similarity	NPD7472	Approved
0.7823	Intermediate Similarity	NPD4060	Phase 1
0.7793	Intermediate Similarity	NPD4908	Phase 1
0.7762	Intermediate Similarity	NPD8651	Approved
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD5588	Approved
0.7692	Intermediate Similarity	NPD7808	Phase 3
0.7677	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.7667	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4538	Approved
0.7667	Intermediate Similarity	NPD4536	Approved
0.7664	Intermediate Similarity	NPD5283	Phase 1
0.766	Intermediate Similarity	NPD5125	Phase 3
0.766	Intermediate Similarity	NPD5126	Approved
0.7633	Intermediate Similarity	NPD7251	Discontinued
0.7632	Intermediate Similarity	NPD5762	Approved
0.7632	Intermediate Similarity	NPD5763	Approved
0.7584	Intermediate Similarity	NPD3620	Phase 2
0.7584	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6797	Phase 2
0.7568	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7157	Approved
0.755	Intermediate Similarity	NPD7097	Phase 1
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6355	Discontinued
0.7533	Intermediate Similarity	NPD5735	Approved
0.7529	Intermediate Similarity	NPD7685	Pre-registration
0.7516	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD4108	Discontinued
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6331	Phase 2
0.7464	Intermediate Similarity	NPD7843	Approved
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7455	Intermediate Similarity	NPD5494	Approved
0.7442	Intermediate Similarity	NPD8313	Approved
0.7442	Intermediate Similarity	NPD8312	Approved
0.7439	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2970	Approved
0.7425	Intermediate Similarity	NPD2969	Approved
0.741	Intermediate Similarity	NPD8127	Discontinued
0.7403	Intermediate Similarity	NPD1375	Discontinued
0.7381	Intermediate Similarity	NPD6166	Phase 2
0.7381	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3018	Phase 2
0.7365	Intermediate Similarity	NPD3051	Approved
0.7362	Intermediate Similarity	NPD2978	Approved
0.7362	Intermediate Similarity	NPD2977	Approved
0.7329	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD5177	Phase 3
0.7305	Intermediate Similarity	NPD6671	Approved
0.7303	Intermediate Similarity	NPD5124	Phase 1
0.7303	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2684	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
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
0.7279	Intermediate Similarity	NPD6696	Suspended
0.7278	Intermediate Similarity	NPD2489	Approved
0.7278	Intermediate Similarity	NPD27	Approved
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7273	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7095	Approved
0.7266	Intermediate Similarity	NPD228	Approved
0.7262	Intermediate Similarity	NPD6071	Discontinued
0.7261	Intermediate Similarity	NPD4110	Phase 3
0.7261	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6653	Approved
0.7244	Intermediate Similarity	NPD2424	Discontinued
0.7241	Intermediate Similarity	NPD7311	Approved
0.7241	Intermediate Similarity	NPD7310	Approved
0.7241	Intermediate Similarity	NPD7312	Approved
0.7241	Intermediate Similarity	NPD7313	Approved
0.7237	Intermediate Similarity	NPD4140	Approved
0.7229	Intermediate Similarity	NPD7075	Discontinued
0.7228	Intermediate Similarity	NPD7680	Approved
0.7226	Intermediate Similarity	NPD290	Approved
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2677	Approved
0.7212	Intermediate Similarity	NPD2563	Approved
0.7212	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2560	Approved
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7211	Intermediate Similarity	NPD5327	Phase 3
0.7211	Intermediate Similarity	NPD2983	Phase 2
0.7211	Intermediate Similarity	NPD2982	Phase 2
0.7205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7309	Approved
0.7197	Intermediate Similarity	NPD4236	Phase 3
0.7197	Intermediate Similarity	NPD4237	Approved
0.7181	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7175	Intermediate Similarity	NPD7906	Approved
0.7175	Intermediate Similarity	NPD6841	Approved
0.7175	Intermediate Similarity	NPD6843	Phase 3
0.7175	Intermediate Similarity	NPD6842	Approved
0.717	Intermediate Similarity	NPD6667	Approved
0.717	Intermediate Similarity	NPD6666	Approved
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7161	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD4535	Phase 3
0.7152	Intermediate Similarity	NPD5773	Approved
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5772	Approved
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2981	Phase 2
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1558	Phase 1
0.7122	Intermediate Similarity	NPD3021	Approved
0.7122	Intermediate Similarity	NPD3022	Approved
0.7119	Intermediate Similarity	NPD4663	Approved
0.7117	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7079	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7028	Phase 2
0.7063	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6516	Phase 2
0.7055	Intermediate Similarity	NPD5846	Approved
0.7045	Intermediate Similarity	NPD4578	Approved
0.7045	Intermediate Similarity	NPD4577	Approved
0.7037	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7526	Approved
0.7037	Intermediate Similarity	NPD52	Approved
0.7032	Intermediate Similarity	NPD6353	Approved
0.703	Intermediate Similarity	NPD6072	Discontinued
0.7019	Intermediate Similarity	NPD7041	Phase 2
0.7019	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1774	Approved
0.7013	Intermediate Similarity	NPD2238	Phase 2
0.7012	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD2161	Phase 2
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6994	Remote Similarity	NPD3751	Discontinued
0.6989	Remote Similarity	NPD7549	Discontinued
0.6988	Remote Similarity	NPD6801	Discontinued
0.6988	Remote Similarity	NPD3383	Approved
0.6988	Remote Similarity	NPD3382	Approved
0.6988	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3384	Approved
0.6987	Remote Similarity	NPD7119	Phase 2
0.6987	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4162	Approved
0.6981	Remote Similarity	NPD3060	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