NPASS Compound

Structure

NPC473288 OpenBabel07101718182D 37 41 0 0 1 0 0 0 0 0999 V2000 -1.3286 -0.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2451 -0.8208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4405 -1.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 -1.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1270 -1.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5329 -1.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1270 -1.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5157 2.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3954 5.4918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4788 5.8842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 -0.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3349 -0.5329 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4671 -1.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1158 1.6361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7096 0.8315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3097 -0.0851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3160 -0.1970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2983 4.4890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7222 0.6076 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3217 4.2738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3286 -0.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.3954 5.4843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8889 6.3615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5790 -2.3286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7033 0.9435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9035 -0.8897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9161 -1.1136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0464 3.8255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8889 6.3541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9218 3.3573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8153 5.1361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1221 1.5241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7285 0.4956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 25 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 34 1 0 0 0 0 9 26 1 0 0 0 0 9 27 1 0 0 0 0 10 26 1 0 0 0 0 10 35 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 6 0 0 0 13 17 1 0 0 0 0 13 28 2 0 0 0 0 14 8 1 6 0 0 0 14 18 1 0 0 0 0 14 36 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 25 1 6 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 29 1 1 0 0 0 19 20 1 0 0 0 0 19 30 1 6 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 1 0 0 0 21 32 1 0 0 0 0 22 36 1 0 0 0 0 22 37 1 6 0 0 0 23 34 1 6 0 0 0 23 35 1 0 0 0 0 24 37 1 0 0 0 0 26 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.26
Volume:	506.889
LogP:	0.863
LogD:	0.233
LogS:	-2.612
# Rotatable Bonds:	7
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	6.531
Fsp3:	0.885
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.591
MDCK Permeability:	2.2195055862539448e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.717
Human Intestinal Absorption (HIA):	0.906
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	72.70439147949219%
Volume Distribution (VD):	0.475
Pgp-substrate:	23.096216201782227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.261
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	1.32
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.312
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.158
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.21

Download Data

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

Natural Product: NPC473288

Natural Product ID:	NPC473288
*Common Name:**	Tinosinenside
IUPAC Name:	n.a.
Synonyms:	Tinosinenside
Standard InCHIKey:	XFLVPLJMLLCEOX-CHGLPPAKSA-N
Standard InCHI:	InChI=1S/C26H40O11/c1-11-7-13(28)17-15-12(5-6-25(17,4)16(11)15)24(2,3)37-22-20(31)19(30)18(29)14(36-22)8-34-23-21(32)26(33,9-27)10-35-23/h7,12,14-23,27,29-33H,5-6,8-10H2,1-4H3/t12-,14-,15?,16+,17-,18-,19+,20-,21+,22+,23-,25?,26-/m1/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](OC([C@@H]2CCC3([C@@H]4C2[C@H]3C(=O)C=C4C)C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398270
PubChem CID:	44445505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15960	Tinospora sinensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18020421]
NPO15960	Tinospora sinensis	Species	Menispermaceae	Eukaryota	Stems	n.a.	n.a.	PMID[28358196]
NPO15960	Tinospora sinensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15960	Tinospora sinensis	Species	Menispermaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1900000.0	nM	PMID[501018]

☑ 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 NPC473288 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	236
0.1-0.2	1467
0.2-0.3	5259
0.3-0.4	10396
0.4-0.5	10447
0.5-0.6	6682
0.6-0.7	5411
0.7-0.8	2583
0.8-0.85	196
0.85-0.9	17
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC70733
0.9	High Similarity	NPC56071
0.8889	High Similarity	NPC108141
0.8857	High Similarity	NPC272576
0.88	High Similarity	NPC256230
0.8774	High Similarity	NPC246205
0.875	High Similarity	NPC100955
0.875	High Similarity	NPC121566
0.8667	High Similarity	NPC63023
0.8667	High Similarity	NPC95243
0.8667	High Similarity	NPC210178
0.8624	High Similarity	NPC62696
0.8624	High Similarity	NPC477944
0.8624	High Similarity	NPC293038
0.8598	High Similarity	NPC118225
0.8585	High Similarity	NPC293512
0.8558	High Similarity	NPC223834
0.8545	High Similarity	NPC102088
0.8529	High Similarity	NPC278506
0.8519	High Similarity	NPC52241
0.8519	High Similarity	NPC154856
0.8519	High Similarity	NPC475317
0.8476	Intermediate Similarity	NPC151516
0.8468	Intermediate Similarity	NPC134869
0.8468	Intermediate Similarity	NPC152199
0.8468	Intermediate Similarity	NPC235539
0.8455	Intermediate Similarity	NPC260665
0.8421	Intermediate Similarity	NPC42675
0.8407	Intermediate Similarity	NPC319570
0.8393	Intermediate Similarity	NPC309433
0.8378	Intermediate Similarity	NPC74727
0.8378	Intermediate Similarity	NPC165439
0.8378	Intermediate Similarity	NPC474906
0.8378	Intermediate Similarity	NPC18547
0.8364	Intermediate Similarity	NPC130427
0.8364	Intermediate Similarity	NPC11252
0.8364	Intermediate Similarity	NPC471967
0.8364	Intermediate Similarity	NPC174836
0.8364	Intermediate Similarity	NPC210420
0.8364	Intermediate Similarity	NPC289312
0.8364	Intermediate Similarity	NPC474265
0.8362	Intermediate Similarity	NPC277191
0.8362	Intermediate Similarity	NPC190846
0.8349	Intermediate Similarity	NPC83005
0.8349	Intermediate Similarity	NPC470065
0.8349	Intermediate Similarity	NPC127153
0.8348	Intermediate Similarity	NPC28532
0.8333	Intermediate Similarity	NPC392
0.8333	Intermediate Similarity	NPC219900
0.8333	Intermediate Similarity	NPC177524
0.8319	Intermediate Similarity	NPC297179
0.8318	Intermediate Similarity	NPC162033
0.8304	Intermediate Similarity	NPC302471
0.8304	Intermediate Similarity	NPC31797
0.8288	Intermediate Similarity	NPC471627
0.8288	Intermediate Similarity	NPC471173
0.8288	Intermediate Similarity	NPC75167
0.8288	Intermediate Similarity	NPC311592
0.8288	Intermediate Similarity	NPC178981
0.8276	Intermediate Similarity	NPC238005
0.8276	Intermediate Similarity	NPC1980
0.8276	Intermediate Similarity	NPC141196
0.8273	Intermediate Similarity	NPC201992
0.8261	Intermediate Similarity	NPC202051
0.8246	Intermediate Similarity	NPC190939
0.8246	Intermediate Similarity	NPC473401
0.8246	Intermediate Similarity	NPC197003
0.8246	Intermediate Similarity	NPC161738
0.8246	Intermediate Similarity	NPC473920
0.8224	Intermediate Similarity	NPC223741
0.8214	Intermediate Similarity	NPC474557
0.8214	Intermediate Similarity	NPC473882
0.8214	Intermediate Similarity	NPC477580
0.8214	Intermediate Similarity	NPC181145
0.8214	Intermediate Similarity	NPC471398
0.8205	Intermediate Similarity	NPC473505
0.819	Intermediate Similarity	NPC216866
0.8182	Intermediate Similarity	NPC27551
0.8182	Intermediate Similarity	NPC129340
0.8182	Intermediate Similarity	NPC101450
0.8182	Intermediate Similarity	NPC114961
0.8174	Intermediate Similarity	NPC241192
0.8174	Intermediate Similarity	NPC48692
0.8165	Intermediate Similarity	NPC295389
0.8165	Intermediate Similarity	NPC94942
0.8158	Intermediate Similarity	NPC188667
0.8158	Intermediate Similarity	NPC176005
0.8158	Intermediate Similarity	NPC204552
0.8142	Intermediate Similarity	NPC251236
0.8142	Intermediate Similarity	NPC279638
0.8142	Intermediate Similarity	NPC96312
0.8142	Intermediate Similarity	NPC40632
0.8142	Intermediate Similarity	NPC328374
0.8136	Intermediate Similarity	NPC198714
0.8136	Intermediate Similarity	NPC285091
0.8136	Intermediate Similarity	NPC93368
0.8136	Intermediate Similarity	NPC47113
0.8136	Intermediate Similarity	NPC174367
0.8125	Intermediate Similarity	NPC293658
0.8125	Intermediate Similarity	NPC73455
0.8125	Intermediate Similarity	NPC51978
0.8125	Intermediate Similarity	NPC474410
0.8125	Intermediate Similarity	NPC200944
0.8125	Intermediate Similarity	NPC49451
0.812	Intermediate Similarity	NPC227397
0.8108	Intermediate Similarity	NPC250481
0.8108	Intermediate Similarity	NPC285410
0.8108	Intermediate Similarity	NPC263827
0.8103	Intermediate Similarity	NPC249553
0.8103	Intermediate Similarity	NPC182900
0.8095	Intermediate Similarity	NPC40182
0.8095	Intermediate Similarity	NPC198422
0.8091	Intermediate Similarity	NPC57362
0.8091	Intermediate Similarity	NPC167383
0.8091	Intermediate Similarity	NPC237503
0.8091	Intermediate Similarity	NPC306746
0.8091	Intermediate Similarity	NPC137917
0.8091	Intermediate Similarity	NPC204407
0.8091	Intermediate Similarity	NPC265655
0.8087	Intermediate Similarity	NPC475775
0.8087	Intermediate Similarity	NPC161065
0.8087	Intermediate Similarity	NPC122971
0.8087	Intermediate Similarity	NPC476529
0.8087	Intermediate Similarity	NPC279143
0.807	Intermediate Similarity	NPC473968
0.8067	Intermediate Similarity	NPC152091
0.8053	Intermediate Similarity	NPC473798
0.8053	Intermediate Similarity	NPC472274
0.8053	Intermediate Similarity	NPC116024
0.8053	Intermediate Similarity	NPC475633
0.8051	Intermediate Similarity	NPC475194
0.8051	Intermediate Similarity	NPC318135
0.8051	Intermediate Similarity	NPC30188
0.8051	Intermediate Similarity	NPC177820
0.8039	Intermediate Similarity	NPC302584
0.8036	Intermediate Similarity	NPC474516
0.8036	Intermediate Similarity	NPC46388
0.8036	Intermediate Similarity	NPC477253
0.8036	Intermediate Similarity	NPC37739
0.8034	Intermediate Similarity	NPC471965
0.8034	Intermediate Similarity	NPC15918
0.8034	Intermediate Similarity	NPC169816
0.8034	Intermediate Similarity	NPC305771
0.8034	Intermediate Similarity	NPC94072
0.802	Intermediate Similarity	NPC473058
0.8019	Intermediate Similarity	NPC167974
0.8018	Intermediate Similarity	NPC474589
0.8018	Intermediate Similarity	NPC475296
0.8018	Intermediate Similarity	NPC220984
0.8018	Intermediate Similarity	NPC279554
0.8018	Intermediate Similarity	NPC29069
0.8018	Intermediate Similarity	NPC136877
0.8018	Intermediate Similarity	NPC56713
0.8018	Intermediate Similarity	NPC199457
0.8018	Intermediate Similarity	NPC102914
0.8018	Intermediate Similarity	NPC474567
0.8018	Intermediate Similarity	NPC476884
0.8018	Intermediate Similarity	NPC476881
0.8018	Intermediate Similarity	NPC476882
0.8018	Intermediate Similarity	NPC174679
0.8018	Intermediate Similarity	NPC476887
0.8018	Intermediate Similarity	NPC108709
0.8018	Intermediate Similarity	NPC75747
0.8018	Intermediate Similarity	NPC90856
0.8018	Intermediate Similarity	NPC269095
0.8018	Intermediate Similarity	NPC476880
0.8018	Intermediate Similarity	NPC110139
0.8018	Intermediate Similarity	NPC164194
0.8018	Intermediate Similarity	NPC7870
0.8018	Intermediate Similarity	NPC270667
0.8018	Intermediate Similarity	NPC476886
0.8018	Intermediate Similarity	NPC127056
0.8018	Intermediate Similarity	NPC78046
0.8018	Intermediate Similarity	NPC59804
0.8018	Intermediate Similarity	NPC274507
0.8018	Intermediate Similarity	NPC68419
0.8018	Intermediate Similarity	NPC476883
0.8018	Intermediate Similarity	NPC476885
0.8017	Intermediate Similarity	NPC107338
0.8017	Intermediate Similarity	NPC112038
0.8017	Intermediate Similarity	NPC308459
0.8017	Intermediate Similarity	NPC109607
0.8	Intermediate Similarity	NPC69273
0.8	Intermediate Similarity	NPC168899
0.8	Intermediate Similarity	NPC239547
0.8	Intermediate Similarity	NPC96597
0.8	Intermediate Similarity	NPC258323
0.8	Intermediate Similarity	NPC234522
0.8	Intermediate Similarity	NPC309503
0.8	Intermediate Similarity	NPC239293
0.8	Intermediate Similarity	NPC177246
0.8	Intermediate Similarity	NPC155319
0.8	Intermediate Similarity	NPC311534
0.8	Intermediate Similarity	NPC475899
0.8	Intermediate Similarity	NPC284807
0.8	Intermediate Similarity	NPC475632
0.8	Intermediate Similarity	NPC28198
0.8	Intermediate Similarity	NPC293850
0.8	Intermediate Similarity	NPC91197
0.8	Intermediate Similarity	NPC125551

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 NPC473288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1716
0.2-0.3	4114
0.3-0.4	2043
0.4-0.5	568
0.5-0.6	240
0.6-0.7	176
0.7-0.8	83
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8762	High Similarity	NPD6412	Phase 2
0.8333	Intermediate Similarity	NPD6686	Approved
0.8034	Intermediate Similarity	NPD6370	Approved
0.7966	Intermediate Similarity	NPD8328	Phase 3
0.7863	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD6059	Approved
0.7833	Intermediate Similarity	NPD7507	Approved
0.7769	Intermediate Similarity	NPD8293	Discontinued
0.7768	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7736	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7642	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD7492	Approved
0.7583	Intermediate Similarity	NPD5988	Approved
0.7565	Intermediate Similarity	NPD6882	Approved
0.7541	Intermediate Similarity	NPD6616	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.7458	Intermediate Similarity	NPD6009	Approved
0.7458	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6319	Approved
0.7414	Intermediate Similarity	NPD8297	Approved
0.7377	Intermediate Similarity	NPD6067	Discontinued
0.735	Intermediate Similarity	NPD4632	Approved
0.735	Intermediate Similarity	NPD8133	Approved
0.7345	Intermediate Similarity	NPD6402	Approved
0.7345	Intermediate Similarity	NPD6675	Approved
0.7345	Intermediate Similarity	NPD7128	Approved
0.7345	Intermediate Similarity	NPD5739	Approved
0.7304	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD6372	Approved
0.728	Intermediate Similarity	NPD6033	Approved
0.725	Intermediate Similarity	NPD7327	Approved
0.725	Intermediate Similarity	NPD7328	Approved
0.7217	Intermediate Similarity	NPD7320	Approved
0.7217	Intermediate Similarity	NPD6899	Approved
0.7217	Intermediate Similarity	NPD6881	Approved
0.7213	Intermediate Similarity	NPD7503	Approved
0.7213	Intermediate Similarity	NPD8517	Approved
0.7213	Intermediate Similarity	NPD8516	Approved
0.7213	Intermediate Similarity	NPD8513	Phase 3
0.7213	Intermediate Similarity	NPD8515	Approved
0.719	Intermediate Similarity	NPD7516	Approved
0.7182	Intermediate Similarity	NPD6083	Phase 2
0.7182	Intermediate Similarity	NPD4755	Approved
0.7182	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD6649	Approved
0.7179	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD5328	Approved
0.7131	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD8294	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7105	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4634	Approved
0.7094	Intermediate Similarity	NPD6883	Approved
0.7094	Intermediate Similarity	NPD7102	Approved
0.7094	Intermediate Similarity	NPD7290	Approved
0.7073	Intermediate Similarity	NPD8379	Approved
0.7073	Intermediate Similarity	NPD8296	Approved
0.7073	Intermediate Similarity	NPD8378	Approved
0.7073	Intermediate Similarity	NPD8380	Approved
0.7073	Intermediate Similarity	NPD8335	Approved
0.7073	Intermediate Similarity	NPD8033	Approved
0.7054	Intermediate Similarity	NPD4700	Approved
0.7054	Intermediate Similarity	NPD5286	Approved
0.7054	Intermediate Similarity	NPD5285	Approved
0.7054	Intermediate Similarity	NPD4696	Approved
0.7043	Intermediate Similarity	NPD6008	Approved
0.7037	Intermediate Similarity	NPD6079	Approved
0.7034	Intermediate Similarity	NPD6869	Approved
0.7034	Intermediate Similarity	NPD8130	Phase 1
0.7034	Intermediate Similarity	NPD6847	Approved
0.7034	Intermediate Similarity	NPD6617	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3133	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.7009	Intermediate Similarity	NPD6012	Approved
0.7009	Intermediate Similarity	NPD4753	Phase 2
0.7009	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD5695	Phase 3
0.6972	Remote Similarity	NPD6399	Phase 3
0.696	Remote Similarity	NPD7604	Phase 2
0.6944	Remote Similarity	NPD46	Approved
0.6944	Remote Similarity	NPD6698	Approved
0.6935	Remote Similarity	NPD5983	Phase 2
0.693	Remote Similarity	NPD5226	Approved
0.693	Remote Similarity	NPD5211	Phase 2
0.693	Remote Similarity	NPD5225	Approved
0.693	Remote Similarity	NPD4633	Approved
0.693	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5282	Discontinued
0.6909	Remote Similarity	NPD7748	Approved
0.6899	Remote Similarity	NPD5956	Approved
0.6897	Remote Similarity	NPD4767	Approved
0.6897	Remote Similarity	NPD4768	Approved
0.6891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6684	Approved
0.6887	Remote Similarity	NPD7521	Approved
0.6887	Remote Similarity	NPD5330	Approved
0.6887	Remote Similarity	NPD7146	Approved
0.6887	Remote Similarity	NPD6409	Approved
0.6887	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD7334	Approved
0.6881	Remote Similarity	NPD7515	Phase 2
0.6881	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD5174	Approved
0.687	Remote Similarity	NPD5175	Approved
0.6857	Remote Similarity	NPD4786	Approved
0.685	Remote Similarity	NPD6336	Discontinued
0.6842	Remote Similarity	NPD5223	Approved
0.6833	Remote Similarity	NPD6053	Discontinued
0.6827	Remote Similarity	NPD3667	Approved
0.6818	Remote Similarity	NPD4202	Approved
0.6814	Remote Similarity	NPD5696	Approved
0.6814	Remote Similarity	NPD7638	Approved
0.681	Remote Similarity	NPD5141	Approved
0.6807	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5222	Approved
0.6786	Remote Similarity	NPD4697	Phase 3
0.6786	Remote Similarity	NPD5221	Approved
0.678	Remote Similarity	NPD4730	Approved
0.678	Remote Similarity	NPD4729	Approved
0.6769	Remote Similarity	NPD6914	Discontinued
0.6759	Remote Similarity	NPD6672	Approved
0.6759	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5737	Approved
0.6759	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD7639	Approved
0.6754	Remote Similarity	NPD7640	Approved
0.6748	Remote Similarity	NPD7115	Discovery
0.6729	Remote Similarity	NPD5279	Phase 3
0.6726	Remote Similarity	NPD5173	Approved
0.6724	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6694	Remote Similarity	NPD7641	Discontinued
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD3573	Approved
0.664	Remote Similarity	NPD7101	Approved
0.664	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD5329	Approved
0.6615	Remote Similarity	NPD8337	Approved
0.6615	Remote Similarity	NPD8336	Approved
0.6614	Remote Similarity	NPD8080	Discontinued
0.6607	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7900	Approved
0.6577	Remote Similarity	NPD5281	Approved
0.6577	Remote Similarity	NPD5284	Approved
0.6577	Remote Similarity	NPD7983	Approved
0.656	Remote Similarity	NPD6335	Approved
0.6555	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6673	Approved
0.6545	Remote Similarity	NPD6080	Approved
0.6545	Remote Similarity	NPD6904	Approved
0.6542	Remote Similarity	NPD4197	Approved
0.6535	Remote Similarity	NPD6909	Approved
0.6535	Remote Similarity	NPD6908	Approved
0.6529	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD4225	Approved
0.6522	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5779	Approved
0.6518	Remote Similarity	NPD5778	Approved
0.648	Remote Similarity	NPD6317	Approved
0.648	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4695	Discontinued
0.6475	Remote Similarity	NPD5217	Approved
0.6475	Remote Similarity	NPD5215	Approved
0.6475	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD6313	Approved
0.6429	Remote Similarity	NPD6050	Approved
0.6429	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD4689	Approved
0.6422	Remote Similarity	NPD4693	Phase 3
0.6422	Remote Similarity	NPD4688	Approved
0.6422	Remote Similarity	NPD4694	Approved
0.6422	Remote Similarity	NPD5690	Phase 2
0.6422	Remote Similarity	NPD5205	Approved
0.6422	Remote Similarity	NPD4623	Approved
0.6422	Remote Similarity	NPD3574	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