NPASS Compound

Structure

NPC64913 OpenBabel07101718332D 30 32 0 0 1 0 0 0 0 0999 V2000 -1.3803 2.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 4.3941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1428 2.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6820 2.8291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2539 -1.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9262 2.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2826 -0.6029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 0.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4507 1.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1463 3.4093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 1.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0566 1.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8350 0.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 1.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4936 -0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0860 3.0673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1107 -0.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0469 1.7628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8521 3.7101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0504 -0.8382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0406 1.9992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4410 1.1139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 2.0825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 -1.0554 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 12 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 27 1 0 0 0 0 12 19 1 0 0 0 0 13 22 1 1 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 1 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 5 1 1 0 0 0 21 30 1 0 0 0 0 22 26 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	417.902
LogP:	3.009
LogD:	2.624
LogS:	-4.012
# Rotatable Bonds:	7
TPSA:	104.43
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	6.033
Fsp3:	0.545
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:	-4.827
MDCK Permeability:	1.737300044624135e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.114
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	83.9035873413086%
Volume Distribution (VD):	1.081
Pgp-substrate:	15.875757217407227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.164
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.537
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.446
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	12.133
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.636
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.926
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.887
Carcinogencity:	0.906
Eye Corrosion:	0.255
Eye Irritation:	0.088
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC64913

Natural Product ID:	NPC64913
*Common Name:**	YWFWDFNNMSZVOA-JXRWWANWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YWFWDFNNMSZVOA-JXRWWANWSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-12(2)19(24)28-16-9-13(3)22(26-6)8-7-21(5,30-22)10-17-18(16)15(20(25)29-17)11-27-14(4)23/h10,13,16H,1,7-9,11H2,2-6H3/b17-10+/t13-,16+,21-,22+/m1/s1
SMILES:	CO[C@@]12CC[C@](O1)(C)/C=C/1C(=C(C(=O)O1)COC(=O)C)[C@H](C[C@H]2C)OC(=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2062867
PubChem CID:	70688595
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO33276	vernonia cinerea	Species	Asteraceae	Eukaryota	flower	n.a.	n.a.	PMID[22850207]

☑ 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	2
Others	4

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	98.8	%	PMID[537396]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	6.3	%	PMID[537396]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1500.0	nM	PMID[537396]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	39.1	%	PMID[537396]
NPT2	Others	Unspecified		Inhibition	=	94.2	%	PMID[537396]
NPT2	Others	Unspecified		IC50	=	13600.0	nM	PMID[537396]

☑ 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 NPC64913 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	225
0.1-0.2	1310
0.2-0.3	5330
0.3-0.4	13895
0.4-0.5	13555
0.5-0.6	6034
0.6-0.7	2153
0.7-0.8	170
0.8-0.85	11
0.85-0.9	5
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242877
0.9535	High Similarity	NPC175842
0.9535	High Similarity	NPC32494
0.9318	High Similarity	NPC470521
0.9205	High Similarity	NPC59646
0.9091	High Similarity	NPC470520
0.8977	High Similarity	NPC3436
0.8864	High Similarity	NPC225283
0.8804	High Similarity	NPC471490
0.8587	High Similarity	NPC471492
0.8539	High Similarity	NPC260343
0.8409	Intermediate Similarity	NPC130030
0.8404	Intermediate Similarity	NPC2666
0.8298	Intermediate Similarity	NPC473333
0.8105	Intermediate Similarity	NPC301596
0.8105	Intermediate Similarity	NPC299396
0.8021	Intermediate Similarity	NPC471462
0.7917	Intermediate Similarity	NPC172998
0.7812	Intermediate Similarity	NPC234339
0.7812	Intermediate Similarity	NPC273197
0.7717	Intermediate Similarity	NPC204048
0.7711	Intermediate Similarity	NPC232812
0.7708	Intermediate Similarity	NPC474338
0.77	Intermediate Similarity	NPC189609
0.77	Intermediate Similarity	NPC291500
0.77	Intermediate Similarity	NPC140591
0.77	Intermediate Similarity	NPC303653
0.77	Intermediate Similarity	NPC197835
0.7619	Intermediate Similarity	NPC64234
0.7619	Intermediate Similarity	NPC37929
0.7596	Intermediate Similarity	NPC38154
0.7582	Intermediate Similarity	NPC475947
0.7579	Intermediate Similarity	NPC80875
0.7556	Intermediate Similarity	NPC141810
0.7553	Intermediate Similarity	NPC469653
0.7553	Intermediate Similarity	NPC469628
0.7553	Intermediate Similarity	NPC475906
0.7553	Intermediate Similarity	NPC471047
0.7553	Intermediate Similarity	NPC469631
0.7553	Intermediate Similarity	NPC471956
0.7526	Intermediate Similarity	NPC140543
0.7423	Intermediate Similarity	NPC471483
0.7423	Intermediate Similarity	NPC189651
0.7423	Intermediate Similarity	NPC475098
0.74	Intermediate Similarity	NPC187268
0.7386	Intermediate Similarity	NPC123360
0.7386	Intermediate Similarity	NPC301525
0.7368	Intermediate Similarity	NPC475902
0.7363	Intermediate Similarity	NPC281949
0.7363	Intermediate Similarity	NPC301477
0.7363	Intermediate Similarity	NPC25684
0.7356	Intermediate Similarity	NPC474758
0.7347	Intermediate Similarity	NPC476267
0.734	Intermediate Similarity	NPC107787
0.734	Intermediate Similarity	NPC469483
0.7333	Intermediate Similarity	NPC617
0.732	Intermediate Similarity	NPC158061
0.7312	Intermediate Similarity	NPC41856
0.7312	Intermediate Similarity	NPC115786
0.7303	Intermediate Similarity	NPC10572
0.7303	Intermediate Similarity	NPC68156
0.7303	Intermediate Similarity	NPC97516
0.7303	Intermediate Similarity	NPC471225
0.73	Intermediate Similarity	NPC153559
0.7294	Intermediate Similarity	NPC265574
0.7294	Intermediate Similarity	NPC470693
0.7283	Intermediate Similarity	NPC173609
0.7273	Intermediate Similarity	NPC329826
0.7273	Intermediate Similarity	NPC469414
0.7263	Intermediate Similarity	NPC475703
0.7262	Intermediate Similarity	NPC472266
0.7245	Intermediate Similarity	NPC156553
0.7234	Intermediate Similarity	NPC78089
0.7234	Intermediate Similarity	NPC471185
0.7234	Intermediate Similarity	NPC215364
0.7228	Intermediate Similarity	NPC279561
0.7228	Intermediate Similarity	NPC473307
0.7228	Intermediate Similarity	NPC124181
0.7228	Intermediate Similarity	NPC90819
0.7228	Intermediate Similarity	NPC203627
0.7212	Intermediate Similarity	NPC305157
0.7212	Intermediate Similarity	NPC307846
0.7209	Intermediate Similarity	NPC469660
0.7204	Intermediate Similarity	NPC475989
0.7204	Intermediate Similarity	NPC475714
0.72	Intermediate Similarity	NPC288350
0.72	Intermediate Similarity	NPC173329
0.72	Intermediate Similarity	NPC230800
0.7188	Intermediate Similarity	NPC476805
0.7188	Intermediate Similarity	NPC475819
0.7176	Intermediate Similarity	NPC276290
0.7174	Intermediate Similarity	NPC471325
0.7174	Intermediate Similarity	NPC42470
0.7172	Intermediate Similarity	NPC473330
0.7172	Intermediate Similarity	NPC469632
0.7172	Intermediate Similarity	NPC473316
0.7172	Intermediate Similarity	NPC256368
0.7159	Intermediate Similarity	NPC476355
0.7159	Intermediate Similarity	NPC470686
0.7158	Intermediate Similarity	NPC284902
0.7158	Intermediate Similarity	NPC305475
0.7158	Intermediate Similarity	NPC475461
0.7158	Intermediate Similarity	NPC279859
0.7158	Intermediate Similarity	NPC261721
0.7158	Intermediate Similarity	NPC50637
0.7158	Intermediate Similarity	NPC471480
0.7158	Intermediate Similarity	NPC38576
0.7157	Intermediate Similarity	NPC469864
0.7157	Intermediate Similarity	NPC469872
0.7143	Intermediate Similarity	NPC166110
0.7143	Intermediate Similarity	NPC191233
0.7143	Intermediate Similarity	NPC261607
0.7143	Intermediate Similarity	NPC270126
0.7143	Intermediate Similarity	NPC111114
0.7143	Intermediate Similarity	NPC178277
0.7143	Intermediate Similarity	NPC300312
0.7143	Intermediate Similarity	NPC70595
0.7143	Intermediate Similarity	NPC74103
0.7143	Intermediate Similarity	NPC150978
0.7143	Intermediate Similarity	NPC284185
0.7143	Intermediate Similarity	NPC123177
0.7113	Intermediate Similarity	NPC166919
0.7111	Intermediate Similarity	NPC171204
0.7111	Intermediate Similarity	NPC315394
0.7111	Intermediate Similarity	NPC476794
0.7111	Intermediate Similarity	NPC141789
0.7111	Intermediate Similarity	NPC476028
0.7111	Intermediate Similarity	NPC470240
0.71	Intermediate Similarity	NPC291709
0.71	Intermediate Similarity	NPC241407
0.71	Intermediate Similarity	NPC471141
0.7097	Intermediate Similarity	NPC474028
0.7097	Intermediate Similarity	NPC35556
0.7097	Intermediate Similarity	NPC474439
0.7087	Intermediate Similarity	NPC98859
0.7087	Intermediate Similarity	NPC469851
0.7087	Intermediate Similarity	NPC219038
0.7087	Intermediate Similarity	NPC4637
0.7083	Intermediate Similarity	NPC478144
0.7083	Intermediate Similarity	NPC478145
0.7083	Intermediate Similarity	NPC160138
0.7083	Intermediate Similarity	NPC471739
0.7083	Intermediate Similarity	NPC476600
0.7079	Intermediate Similarity	NPC329852
0.7071	Intermediate Similarity	NPC248193
0.7065	Intermediate Similarity	NPC281132
0.7065	Intermediate Similarity	NPC223904
0.7059	Intermediate Similarity	NPC474440
0.7059	Intermediate Similarity	NPC208233
0.7053	Intermediate Similarity	NPC470755
0.7053	Intermediate Similarity	NPC255307
0.7048	Intermediate Similarity	NPC471143
0.7048	Intermediate Similarity	NPC477510
0.7041	Intermediate Similarity	NPC475995
0.7041	Intermediate Similarity	NPC474098
0.7041	Intermediate Similarity	NPC475748
0.7041	Intermediate Similarity	NPC253144
0.7041	Intermediate Similarity	NPC312042
0.7033	Intermediate Similarity	NPC474005
0.7033	Intermediate Similarity	NPC128276
0.703	Intermediate Similarity	NPC16967
0.703	Intermediate Similarity	NPC35498
0.7024	Intermediate Similarity	NPC220766
0.7021	Intermediate Similarity	NPC318468
0.7021	Intermediate Similarity	NPC474193
0.7021	Intermediate Similarity	NPC12283
0.7021	Intermediate Similarity	NPC170286
0.7021	Intermediate Similarity	NPC53867
0.7019	Intermediate Similarity	NPC471599
0.701	Intermediate Similarity	NPC472378
0.701	Intermediate Similarity	NPC233997
0.7	Intermediate Similarity	NPC477131
0.7	Intermediate Similarity	NPC167219
0.7	Intermediate Similarity	NPC191521
0.7	Intermediate Similarity	NPC235906
0.7	Intermediate Similarity	NPC474247
0.6989	Remote Similarity	NPC184208
0.6989	Remote Similarity	NPC325031
0.6989	Remote Similarity	NPC112868
0.6989	Remote Similarity	NPC474894
0.6989	Remote Similarity	NPC471552
0.6989	Remote Similarity	NPC473339
0.6989	Remote Similarity	NPC8538
0.6989	Remote Similarity	NPC59994
0.6989	Remote Similarity	NPC315731
0.6989	Remote Similarity	NPC475481
0.6989	Remote Similarity	NPC79277
0.6989	Remote Similarity	NPC78677
0.6979	Remote Similarity	NPC162071
0.6979	Remote Similarity	NPC291712
0.6979	Remote Similarity	NPC150755
0.697	Remote Similarity	NPC2882
0.697	Remote Similarity	NPC193396
0.697	Remote Similarity	NPC20713
0.697	Remote Similarity	NPC32944
0.6966	Remote Similarity	NPC259599
0.6966	Remote Similarity	NPC294434
0.6966	Remote Similarity	NPC15499
0.6966	Remote Similarity	NPC140287
0.6966	Remote Similarity	NPC117746

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 NPC64913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1759
0.2-0.3	4004
0.3-0.4	2360
0.4-0.5	626
0.5-0.6	187
0.6-0.7	28
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7041	Intermediate Similarity	NPD7838	Discovery
0.6915	Remote Similarity	NPD5209	Approved
0.6893	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1695	Approved
0.6571	Remote Similarity	NPD4225	Approved
0.6562	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6686	Approved
0.6373	Remote Similarity	NPD6698	Approved
0.6373	Remote Similarity	NPD46	Approved
0.6364	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6648	Approved
0.6346	Remote Similarity	NPD5282	Discontinued
0.6327	Remote Similarity	NPD7154	Phase 3
0.6311	Remote Similarity	NPD7983	Approved
0.63	Remote Similarity	NPD4249	Approved
0.6238	Remote Similarity	NPD4250	Approved
0.6238	Remote Similarity	NPD4251	Approved
0.6226	Remote Similarity	NPD7839	Suspended
0.6214	Remote Similarity	NPD5785	Approved
0.62	Remote Similarity	NPD1694	Approved
0.62	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7503	Approved
0.614	Remote Similarity	NPD6371	Approved
0.6095	Remote Similarity	NPD5779	Approved
0.6095	Remote Similarity	NPD5778	Approved
0.6087	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5363	Approved
0.6034	Remote Similarity	NPD6053	Discontinued
0.6033	Remote Similarity	NPD8516	Approved
0.6033	Remote Similarity	NPD8517	Approved
0.6033	Remote Similarity	NPD8515	Approved
0.6033	Remote Similarity	NPD8513	Phase 3
0.602	Remote Similarity	NPD4821	Approved
0.602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4822	Approved
0.602	Remote Similarity	NPD4820	Approved
0.602	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD8039	Approved
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7328	Approved
0.5917	Remote Similarity	NPD7327	Approved
0.5902	Remote Similarity	NPD8033	Approved
0.5876	Remote Similarity	NPD4756	Discovery
0.5868	Remote Similarity	NPD7516	Approved
0.5862	Remote Similarity	NPD2067	Discontinued
0.5849	Remote Similarity	NPD6411	Approved
0.5842	Remote Similarity	NPD5362	Discontinued
0.5833	Remote Similarity	NPD7505	Discontinued
0.5827	Remote Similarity	NPD7319	Approved
0.582	Remote Similarity	NPD8294	Approved
0.582	Remote Similarity	NPD8377	Approved
0.5816	Remote Similarity	NPD4271	Approved
0.5816	Remote Similarity	NPD4268	Approved
0.581	Remote Similarity	NPD6051	Approved
0.5806	Remote Similarity	NPD7829	Approved
0.5806	Remote Similarity	NPD7830	Approved
0.58	Remote Similarity	NPD5369	Approved
0.5794	Remote Similarity	NPD8074	Phase 3
0.5778	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD8378	Approved
0.5772	Remote Similarity	NPD8380	Approved
0.5772	Remote Similarity	NPD8296	Approved
0.5772	Remote Similarity	NPD8379	Approved
0.5772	Remote Similarity	NPD8335	Approved
0.5758	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4270	Approved
0.5743	Remote Similarity	NPD4269	Approved
0.5714	Remote Similarity	NPD7507	Approved
0.5702	Remote Similarity	NPD7115	Discovery
0.5686	Remote Similarity	NPD5332	Approved
0.5686	Remote Similarity	NPD5331	Approved
0.5676	Remote Similarity	NPD7638	Approved
0.5673	Remote Similarity	NPD5786	Approved
0.5644	Remote Similarity	NPD4790	Discontinued
0.5631	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6882	Approved
0.563	Remote Similarity	NPD969	Suspended
0.5625	Remote Similarity	NPD7640	Approved
0.5625	Remote Similarity	NPD7639	Approved
0.5618	Remote Similarity	NPD1145	Discontinued
0.5607	Remote Similarity	NPD5207	Approved
0.5603	Remote Similarity	NPD5954	Clinical (unspecified phase)

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