NPASS Compound

Structure

NPC221993 OpenBabel07101719252D 29 32 0 0 1 0 0 0 0 0999 V2000 1.7796 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -5.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2796 -2.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7796 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8735 3.1336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1691 -0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.9067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 -2.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1473 0.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7796 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 -3.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8904 -0.5841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1303 2.4644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -3.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2518 1.0796 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 6 0 0 0 15 24 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 20 1 0 0 0 0 17 27 1 1 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 22 1 6 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 21 23 1 6 0 0 0 22 11 1 6 0 0 0 22 29 1 0 0 0 0 23 12 1 1 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.25
Volume:	419.607
LogP:	4.147
LogD:	3.535
LogS:	-4.991
# Rotatable Bonds:	3
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	5.552
Fsp3:	0.913
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.707
MDCK Permeability:	3.290612585260533e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.428

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157
Plasma Protein Binding (PPB):	71.77059173583984%
Volume Distribution (VD):	1.012
Pgp-substrate:	19.55797004699707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.216
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.544

ADMET: Excretion

Clearance (CL):	6.024
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.463
AMES Toxicity:	0.941
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.548
Carcinogencity:	0.756
Eye Corrosion:	0.165
Eye Irritation:	0.038
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC221993

Natural Product ID:	NPC221993
*Common Name:**	Negundoin D
IUPAC Name:	n.a.
Synonyms:	Negundoin D
Standard InCHIKey:	GCQMZZDJVNUQJV-WDYVTMJNSA-N
Standard InCHI:	InChI=1S/C23H36O6/c1-14-7-8-16-20(3,4)17(27-15(2)24)9-10-21(16,5)23(14)12-11-22(29-23)13-18(25)28-19(22)26-6/h14,16-17,19H,7-13H2,1-6H3/t14-,16+,17+,19+,21+,22+,23-/m1/s1
SMILES:	CO[C@H]1OC(=O)C[C@]21CC[C@@]1(O2)[C@H](C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL602329
PubChem CID:	46229720
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4390.0	nM	PMID[496350]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	62.03	%	PMID[496350]

☑ 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 NPC221993 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	448
0.1-0.2	3816
0.2-0.3	9195
0.3-0.4	13277
0.4-0.5	6430
0.5-0.6	5771
0.6-0.7	3325
0.7-0.8	379
0.8-0.85	44
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC65133
0.9024	High Similarity	NPC471217
0.9024	High Similarity	NPC471216
0.8916	High Similarity	NPC71541
0.8851	High Similarity	NPC471221
0.8837	High Similarity	NPC474008
0.8696	High Similarity	NPC266417
0.8675	High Similarity	NPC474754
0.8587	High Similarity	NPC475765
0.8587	High Similarity	NPC475785
0.8556	High Similarity	NPC475878
0.8391	Intermediate Similarity	NPC18953
0.8353	Intermediate Similarity	NPC134227
0.8295	Intermediate Similarity	NPC478111
0.8293	Intermediate Similarity	NPC55508
0.8261	Intermediate Similarity	NPC475307
0.8222	Intermediate Similarity	NPC470872
0.8152	Intermediate Similarity	NPC216137
0.814	Intermediate Similarity	NPC60568
0.8111	Intermediate Similarity	NPC62202
0.8111	Intermediate Similarity	NPC110365
0.8111	Intermediate Similarity	NPC213658
0.8111	Intermediate Similarity	NPC45833
0.809	Intermediate Similarity	NPC235402
0.8043	Intermediate Similarity	NPC470114
0.8022	Intermediate Similarity	NPC476435
0.8	Intermediate Similarity	NPC477441
0.8	Intermediate Similarity	NPC471411
0.8	Intermediate Similarity	NPC193785
0.8	Intermediate Similarity	NPC116683
0.8	Intermediate Similarity	NPC471410
0.7978	Intermediate Similarity	NPC79308
0.7978	Intermediate Similarity	NPC477434
0.7959	Intermediate Similarity	NPC80640
0.7959	Intermediate Similarity	NPC244969
0.7959	Intermediate Similarity	NPC213528
0.7955	Intermediate Similarity	NPC13494
0.7952	Intermediate Similarity	NPC109510
0.7952	Intermediate Similarity	NPC474755
0.7938	Intermediate Similarity	NPC80417
0.7931	Intermediate Similarity	NPC475456
0.7931	Intermediate Similarity	NPC125366
0.7921	Intermediate Similarity	NPC207693
0.7872	Intermediate Similarity	NPC35164
0.7872	Intermediate Similarity	NPC474379
0.7865	Intermediate Similarity	NPC476721
0.7843	Intermediate Similarity	NPC22709
0.7835	Intermediate Similarity	NPC472144
0.781	Intermediate Similarity	NPC79193
0.7802	Intermediate Similarity	NPC476717
0.78	Intermediate Similarity	NPC267637
0.78	Intermediate Similarity	NPC100078
0.7791	Intermediate Similarity	NPC143250
0.7778	Intermediate Similarity	NPC82492
0.7778	Intermediate Similarity	NPC51135
0.7778	Intermediate Similarity	NPC473299
0.7778	Intermediate Similarity	NPC101138
0.7778	Intermediate Similarity	NPC25802
0.7767	Intermediate Similarity	NPC470622
0.7742	Intermediate Similarity	NPC477440
0.7742	Intermediate Similarity	NPC477443
0.7742	Intermediate Similarity	NPC472234
0.7742	Intermediate Similarity	NPC472233
0.7732	Intermediate Similarity	NPC472273
0.7732	Intermediate Similarity	NPC472145
0.7723	Intermediate Similarity	NPC166079
0.7723	Intermediate Similarity	NPC184805
0.7723	Intermediate Similarity	NPC273189
0.7723	Intermediate Similarity	NPC306776
0.7708	Intermediate Similarity	NPC21897
0.7692	Intermediate Similarity	NPC477445
0.7692	Intermediate Similarity	NPC272242
0.7677	Intermediate Similarity	NPC178853
0.7674	Intermediate Similarity	NPC107963
0.7667	Intermediate Similarity	NPC474253
0.7667	Intermediate Similarity	NPC474346
0.7667	Intermediate Similarity	NPC475820
0.7667	Intermediate Similarity	NPC213737
0.7667	Intermediate Similarity	NPC474284
0.766	Intermediate Similarity	NPC477444
0.766	Intermediate Similarity	NPC477433
0.766	Intermediate Similarity	NPC18536
0.766	Intermediate Similarity	NPC477442
0.766	Intermediate Similarity	NPC50443
0.7647	Intermediate Similarity	NPC471430
0.764	Intermediate Similarity	NPC475743
0.764	Intermediate Similarity	NPC260977
0.764	Intermediate Similarity	NPC30443
0.764	Intermediate Similarity	NPC285480
0.764	Intermediate Similarity	NPC45256
0.7629	Intermediate Similarity	NPC145553
0.7624	Intermediate Similarity	NPC244247
0.7624	Intermediate Similarity	NPC469827
0.7624	Intermediate Similarity	NPC88469
0.7619	Intermediate Similarity	NPC157571
0.7614	Intermediate Similarity	NPC477287
0.7586	Intermediate Similarity	NPC471151
0.7586	Intermediate Similarity	NPC307865
0.7573	Intermediate Similarity	NPC469826
0.7556	Intermediate Similarity	NPC477284
0.7556	Intermediate Similarity	NPC2096
0.7556	Intermediate Similarity	NPC208912
0.7553	Intermediate Similarity	NPC471459
0.7553	Intermediate Similarity	NPC67653
0.7551	Intermediate Similarity	NPC74466
0.7551	Intermediate Similarity	NPC470632
0.7547	Intermediate Similarity	NPC102619
0.7529	Intermediate Similarity	NPC123122
0.7528	Intermediate Similarity	NPC472951
0.7528	Intermediate Similarity	NPC472943
0.7526	Intermediate Similarity	NPC215570
0.7524	Intermediate Similarity	NPC473062
0.7524	Intermediate Similarity	NPC469824
0.75	Intermediate Similarity	NPC87393
0.75	Intermediate Similarity	NPC179429
0.75	Intermediate Similarity	NPC122083
0.75	Intermediate Similarity	NPC182740
0.75	Intermediate Similarity	NPC211845
0.75	Intermediate Similarity	NPC256104
0.75	Intermediate Similarity	NPC472231
0.75	Intermediate Similarity	NPC472232
0.7476	Intermediate Similarity	NPC203974
0.7476	Intermediate Similarity	NPC126753
0.7475	Intermediate Similarity	NPC292775
0.7473	Intermediate Similarity	NPC15091
0.7451	Intermediate Similarity	NPC470167
0.7449	Intermediate Similarity	NPC235109
0.7449	Intermediate Similarity	NPC203434
0.7449	Intermediate Similarity	NPC476728
0.7449	Intermediate Similarity	NPC238796
0.7449	Intermediate Similarity	NPC237071
0.7447	Intermediate Similarity	NPC56777
0.7447	Intermediate Similarity	NPC476379
0.7447	Intermediate Similarity	NPC201607
0.7447	Intermediate Similarity	NPC33398
0.7444	Intermediate Similarity	NPC470154
0.7439	Intermediate Similarity	NPC84562
0.7429	Intermediate Similarity	NPC49730
0.7429	Intermediate Similarity	NPC98069
0.7429	Intermediate Similarity	NPC101450
0.7429	Intermediate Similarity	NPC66513
0.7429	Intermediate Similarity	NPC98633
0.7426	Intermediate Similarity	NPC470172
0.7426	Intermediate Similarity	NPC471254
0.7423	Intermediate Similarity	NPC477495
0.7423	Intermediate Similarity	NPC470424
0.7419	Intermediate Similarity	NPC114378
0.7419	Intermediate Similarity	NPC103782
0.7416	Intermediate Similarity	NPC73013
0.7407	Intermediate Similarity	NPC475490
0.7404	Intermediate Similarity	NPC224414
0.74	Intermediate Similarity	NPC477656
0.7396	Intermediate Similarity	NPC474065
0.7396	Intermediate Similarity	NPC474631
0.7391	Intermediate Similarity	NPC471044
0.7391	Intermediate Similarity	NPC473336
0.7391	Intermediate Similarity	NPC181871
0.7391	Intermediate Similarity	NPC9060
0.7383	Intermediate Similarity	NPC285086
0.7374	Intermediate Similarity	NPC113976
0.7374	Intermediate Similarity	NPC198549
0.7374	Intermediate Similarity	NPC253586
0.7368	Intermediate Similarity	NPC471222
0.7368	Intermediate Similarity	NPC77001
0.7368	Intermediate Similarity	NPC61688
0.7368	Intermediate Similarity	NPC253618
0.7368	Intermediate Similarity	NPC200580
0.7363	Intermediate Similarity	NPC311642
0.7363	Intermediate Similarity	NPC477446
0.7363	Intermediate Similarity	NPC164289
0.7363	Intermediate Similarity	NPC470155
0.7363	Intermediate Similarity	NPC102156
0.7363	Intermediate Similarity	NPC477447
0.7363	Intermediate Similarity	NPC100366
0.7363	Intermediate Similarity	NPC242771
0.7363	Intermediate Similarity	NPC148740
0.7358	Intermediate Similarity	NPC471251
0.7353	Intermediate Similarity	NPC107385
0.7353	Intermediate Similarity	NPC473406
0.7353	Intermediate Similarity	NPC471253
0.7353	Intermediate Similarity	NPC34562
0.7347	Intermediate Similarity	NPC82633
0.734	Intermediate Similarity	NPC252714
0.7333	Intermediate Similarity	NPC471250
0.7333	Intermediate Similarity	NPC228190
0.7333	Intermediate Similarity	NPC1882
0.7333	Intermediate Similarity	NPC236753
0.7333	Intermediate Similarity	NPC469825
0.7327	Intermediate Similarity	NPC477172
0.7326	Intermediate Similarity	NPC476718
0.732	Intermediate Similarity	NPC472237
0.732	Intermediate Similarity	NPC472238
0.732	Intermediate Similarity	NPC476189
0.732	Intermediate Similarity	NPC12297
0.7315	Intermediate Similarity	NPC477465
0.7312	Intermediate Similarity	NPC474572
0.7312	Intermediate Similarity	NPC476715
0.7312	Intermediate Similarity	NPC473350
0.7308	Intermediate Similarity	NPC293512
0.7308	Intermediate Similarity	NPC96333

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 NPC221993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	467
0.1-0.2	3908
0.2-0.3	3155
0.3-0.4	953
0.4-0.5	349
0.5-0.6	240
0.6-0.7	74
0.7-0.8	4
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
0.764	Intermediate Similarity	NPD1780	Approved
0.764	Intermediate Similarity	NPD1779	Approved
0.7157	Intermediate Similarity	NPD1700	Approved
0.7115	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3669	Approved
0.7059	Intermediate Similarity	NPD229	Approved
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6697	Approved
0.6923	Remote Similarity	NPD6118	Approved
0.6923	Remote Similarity	NPD6114	Approved
0.6923	Remote Similarity	NPD6115	Approved
0.6875	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6116	Phase 1
0.678	Remote Similarity	NPD8293	Discontinued
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8133	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.6723	Remote Similarity	NPD7736	Approved
0.6706	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2686	Approved
0.6705	Remote Similarity	NPD2687	Approved
0.6705	Remote Similarity	NPD2254	Approved
0.6703	Remote Similarity	NPD6117	Approved
0.6636	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8171	Discontinued
0.6629	Remote Similarity	NPD5777	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6529	Remote Similarity	NPD7319	Approved
0.6525	Remote Similarity	NPD8328	Phase 3
0.6514	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7078	Approved
0.6491	Remote Similarity	NPD6940	Discontinued
0.6484	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6686	Approved
0.6422	Remote Similarity	NPD6008	Approved
0.6421	Remote Similarity	NPD6928	Phase 2
0.6417	Remote Similarity	NPD7507	Approved
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6412	Phase 2
0.6356	Remote Similarity	NPD6015	Approved
0.6356	Remote Similarity	NPD6016	Approved
0.6339	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1811	Approved
0.6304	Remote Similarity	NPD1810	Approved
0.6303	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3703	Phase 2
0.6237	Remote Similarity	NPD3702	Approved
0.6211	Remote Similarity	NPD4802	Phase 2
0.6211	Remote Similarity	NPD4238	Approved
0.6154	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD8082	Approved
0.6147	Remote Similarity	NPD8083	Approved
0.6147	Remote Similarity	NPD8138	Approved
0.6147	Remote Similarity	NPD8085	Approved
0.6147	Remote Similarity	NPD8086	Approved
0.6147	Remote Similarity	NPD8084	Approved
0.6147	Remote Similarity	NPD8139	Approved
0.6116	Remote Similarity	NPD6067	Discontinued
0.6102	Remote Similarity	NPD7327	Approved
0.6102	Remote Similarity	NPD7328	Approved
0.6095	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7900	Approved
0.6091	Remote Similarity	NPD8275	Approved
0.6091	Remote Similarity	NPD8276	Approved
0.6087	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD6921	Approved
0.6083	Remote Similarity	NPD8513	Phase 3
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8517	Approved
0.605	Remote Similarity	NPD7516	Approved
0.6048	Remote Similarity	NPD6033	Approved
0.6044	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD8081	Approved
0.6019	Remote Similarity	NPD4225	Approved
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD8301	Approved
0.6	Remote Similarity	NPD8300	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD8377	Approved
0.5982	Remote Similarity	NPD8393	Approved
0.595	Remote Similarity	NPD8033	Approved
0.595	Remote Similarity	NPD8335	Approved
0.595	Remote Similarity	NPD8379	Approved
0.595	Remote Similarity	NPD8296	Approved
0.595	Remote Similarity	NPD8378	Approved
0.595	Remote Similarity	NPD8380	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5360	Phase 3
0.5934	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7902	Approved
0.5914	Remote Similarity	NPD6081	Approved
0.5889	Remote Similarity	NPD4224	Phase 2
0.5882	Remote Similarity	NPD7115	Discovery
0.5877	Remote Similarity	NPD7320	Approved
0.5872	Remote Similarity	NPD7638	Approved
0.587	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5739	Approved
0.5841	Remote Similarity	NPD6402	Approved
0.5841	Remote Similarity	NPD7128	Approved
0.5841	Remote Similarity	NPD6675	Approved
0.5826	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD6372	Approved
0.5818	Remote Similarity	NPD7640	Approved
0.5818	Remote Similarity	NPD7639	Approved
0.5812	Remote Similarity	NPD8297	Approved
0.5806	Remote Similarity	NPD4244	Approved
0.5806	Remote Similarity	NPD4245	Approved
0.5794	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD8307	Discontinued
0.5789	Remote Similarity	NPD8140	Approved
0.5778	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6903	Approved
0.5763	Remote Similarity	NPD4632	Approved
0.5741	Remote Similarity	NPD7991	Discontinued
0.5739	Remote Similarity	NPD6899	Approved
0.5739	Remote Similarity	NPD6881	Approved
0.5728	Remote Similarity	NPD7334	Approved
0.5728	Remote Similarity	NPD6684	Approved
0.5728	Remote Similarity	NPD5330	Approved
0.5728	Remote Similarity	NPD6409	Approved
0.5728	Remote Similarity	NPD7146	Approved
0.5728	Remote Similarity	NPD7521	Approved
0.5726	Remote Similarity	NPD6649	Approved
0.5726	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD7632	Discontinued
0.5699	Remote Similarity	NPD3698	Phase 2
0.5691	Remote Similarity	NPD7503	Approved
0.569	Remote Similarity	NPD8306	Approved
0.569	Remote Similarity	NPD8305	Approved
0.5676	Remote Similarity	NPD8418	Phase 2
0.5667	Remote Similarity	NPD371	Approved
0.5652	Remote Similarity	NPD5697	Approved
0.5652	Remote Similarity	NPD5701	Approved
0.5648	Remote Similarity	NPD6001	Approved
0.5648	Remote Similarity	NPD5282	Discontinued
0.5641	Remote Similarity	NPD8087	Discontinued
0.5641	Remote Similarity	NPD7290	Approved
0.5641	Remote Similarity	NPD6883	Approved
0.5641	Remote Similarity	NPD7102	Approved
0.5638	Remote Similarity	NPD4789	Approved
0.5631	Remote Similarity	NPD1694	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7515	Phase 2
0.56	Remote Similarity	NPD7604	Phase 2

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