NPASS Compound

Structure

NPC294330 OpenBabel07101719522D 45 47 0 0 1 0 0 0 0 0999 V2000 1.6674 5.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8661 3.9832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0858 -1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2382 -3.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 2.6669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6076 4.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1877 -0.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4342 -0.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3583 -1.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3370 -1.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 3.5444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 -1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2832 3.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 -0.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 -0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7348 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3051 -1.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9649 -0.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 1.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 2.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9207 4.2365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2382 -2.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3543 3.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4089 3.1056 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6953 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7348 1.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 1.6708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 -0.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4007 0.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7209 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2700 -1.2462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5825 1.6708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 2.6495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 -1.2655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 1.3126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8668 -1.1902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6102 -2.1639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 2 0 0 0 0 6 24 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 13 1 0 0 0 0 11 22 2 0 0 0 0 12 15 1 0 0 0 0 12 23 2 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 35 1 0 0 0 0 19 25 2 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 21 37 1 0 0 0 0 24 26 1 0 0 0 0 25 31 1 0 0 0 0 26 13 1 6 0 0 0 27 15 1 6 0 0 0 27 36 1 0 0 0 0 28 29 2 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 31 1 0 0 0 0 30 32 2 0 0 0 0 30 33 1 0 0 0 0 31 41 2 0 0 0 0 32 37 1 0 0 0 0 32 42 1 0 0 0 0 33 38 1 0 0 0 0 33 43 2 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 35 45 1 0 0 0 0 36 38 1 0 0 0 0 37 20 1 6 0 0 0 38 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.37
Volume:	675.302
LogP:	7.021
LogD:	4.25
LogS:	-4.198
# Rotatable Bonds:	12
TPSA:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	5.818
Fsp3:	0.579
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152
MDCK Permeability:	1.2002699804725125e-05
Pgp-inhibitor:	0.254
Pgp-substrate:	0.689
Human Intestinal Absorption (HIA):	0.252
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.662

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	98.26799011230469%
Volume Distribution (VD):	1.299
Pgp-substrate:	2.811335325241089%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.535
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	13.365
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.061
Carcinogencity:	0.551
Eye Corrosion:	0.107
Eye Irritation:	0.466
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC294330

Natural Product ID:	NPC294330
*Common Name:**	Garcimultiflorone D
IUPAC Name:	n.a.
Synonyms:	Garcimultiflorone D
Standard InCHIKey:	BWJVAZLOCUCVOO-DDFNXOHMSA-N
Standard InCHI:	InChI=1S/C38H52O7/c1-22(2)11-13-26(24(5)6)20-37-21-27(15-12-23(3)4)36(9,10)38(34(37)44,18-17-35(7,8)45)33(43)30(32(37)42)31(41)25-14-16-28(39)29(40)19-25/h11-12,14,16,19,26-27,39-40,42,45H,5,13,15,17-18,20-21H2,1-4,6-10H3/t26-,27-,37-,38+/m1/s1
SMILES:	CC(=CC[C@H](C[C@@]12C[C@@H](CC=C(C)C)C(C)(C)[C@@](CCC(C)(C)O)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)O)O)C2=O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215427
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	stems	n.a.	n.a.	PMID[12932126]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20681570]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	Twigs and leaves	Taichung, Taiwan	1993-Aug	PMID[9322359]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5049	Garcinia multiflora	Species	Clusiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17500.0	nM	PMID[534544]
NPT2	Others	Unspecified		Ratio	<=	3.0	n.a.	PMID[534544]
NPT2	Others	Unspecified		Ratio	>	3.0	n.a.	PMID[534544]

☑ 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 NPC294330 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	370
0.1-0.2	1503
0.2-0.3	2991
0.3-0.4	7756
0.4-0.5	11035
0.5-0.6	6618
0.6-0.7	9952
0.7-0.8	2323
0.8-0.85	84
0.85-0.9	14
0.9-0.95	16
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC297797
0.9924	High Similarity	NPC289358
0.9924	High Similarity	NPC50615
0.9924	High Similarity	NPC477849
0.9924	High Similarity	NPC28592
0.9924	High Similarity	NPC5014
0.9924	High Similarity	NPC42384
0.9924	High Similarity	NPC149773
0.9924	High Similarity	NPC473779
0.9924	High Similarity	NPC469857
0.9924	High Similarity	NPC46242
0.9924	High Similarity	NPC165191
0.9924	High Similarity	NPC51531
0.9924	High Similarity	NPC114333
0.9924	High Similarity	NPC23667
0.9924	High Similarity	NPC473479
0.9924	High Similarity	NPC91887
0.9924	High Similarity	NPC157284
0.9924	High Similarity	NPC245760
0.9776	High Similarity	NPC473527
0.9773	High Similarity	NPC7464
0.9635	High Similarity	NPC294679
0.9635	High Similarity	NPC145301
0.9635	High Similarity	NPC8493
0.9635	High Similarity	NPC144247
0.9635	High Similarity	NPC469856
0.9635	High Similarity	NPC469375
0.9635	High Similarity	NPC469854
0.9632	High Similarity	NPC30846
0.9632	High Similarity	NPC469855
0.9632	High Similarity	NPC471972
0.9632	High Similarity	NPC471971
0.9496	High Similarity	NPC471970
0.9481	High Similarity	NPC469680
0.9481	High Similarity	NPC471974
0.9481	High Similarity	NPC469681
0.9362	High Similarity	NPC132810
0.9242	High Similarity	NPC25736
0.9225	High Similarity	NPC264229
0.9225	High Similarity	NPC46549
0.922	High Similarity	NPC273798
0.9161	High Similarity	NPC237441
0.9041	High Similarity	NPC305710
0.8966	High Similarity	NPC48949
0.8849	High Similarity	NPC118366
0.8832	High Similarity	NPC138472
0.8832	High Similarity	NPC4170
0.8832	High Similarity	NPC474715
0.8714	High Similarity	NPC277559
0.8696	High Similarity	NPC111845
0.8667	High Similarity	NPC471968
0.8652	High Similarity	NPC230811
0.8613	High Similarity	NPC117609
0.8603	High Similarity	NPC234175
0.8582	High Similarity	NPC49911
0.8571	High Similarity	NPC43353
0.8571	High Similarity	NPC153088
0.8561	High Similarity	NPC294226
0.8531	High Similarity	NPC470035
0.8493	Intermediate Similarity	NPC470038
0.8483	Intermediate Similarity	NPC199936
0.844	Intermediate Similarity	NPC258502
0.8414	Intermediate Similarity	NPC184935
0.8403	Intermediate Similarity	NPC471853
0.8403	Intermediate Similarity	NPC476534
0.8394	Intermediate Similarity	NPC72667
0.8392	Intermediate Similarity	NPC416
0.8392	Intermediate Similarity	NPC61398
0.838	Intermediate Similarity	NPC474311
0.8378	Intermediate Similarity	NPC10842
0.8367	Intermediate Similarity	NPC258856
0.8345	Intermediate Similarity	NPC108129
0.8333	Intermediate Similarity	NPC472903
0.8322	Intermediate Similarity	NPC471152
0.8321	Intermediate Similarity	NPC254492
0.8321	Intermediate Similarity	NPC15837
0.831	Intermediate Similarity	NPC72918
0.8288	Intermediate Similarity	NPC291078
0.8288	Intermediate Similarity	NPC169214
0.8288	Intermediate Similarity	NPC229218
0.8288	Intermediate Similarity	NPC192597
0.8288	Intermediate Similarity	NPC248068
0.8288	Intermediate Similarity	NPC176030
0.8288	Intermediate Similarity	NPC141817
0.8273	Intermediate Similarity	NPC171460
0.8261	Intermediate Similarity	NPC84672
0.8261	Intermediate Similarity	NPC69424
0.8261	Intermediate Similarity	NPC176130
0.8261	Intermediate Similarity	NPC78364
0.8261	Intermediate Similarity	NPC324209
0.8258	Intermediate Similarity	NPC150919
0.8255	Intermediate Similarity	NPC52692
0.8243	Intermediate Similarity	NPC75295
0.8239	Intermediate Similarity	NPC202225
0.8231	Intermediate Similarity	NPC224884
0.8231	Intermediate Similarity	NPC209085
0.8219	Intermediate Similarity	NPC472904
0.8212	Intermediate Similarity	NPC470037
0.8201	Intermediate Similarity	NPC96024
0.8194	Intermediate Similarity	NPC147418
0.8194	Intermediate Similarity	NPC475957
0.8194	Intermediate Similarity	NPC264022
0.8194	Intermediate Similarity	NPC290030
0.8182	Intermediate Similarity	NPC80035
0.8176	Intermediate Similarity	NPC470377
0.8176	Intermediate Similarity	NPC478059
0.8176	Intermediate Similarity	NPC478060
0.8176	Intermediate Similarity	NPC471975
0.8176	Intermediate Similarity	NPC470374
0.8175	Intermediate Similarity	NPC199273
0.8175	Intermediate Similarity	NPC15127
0.8169	Intermediate Similarity	NPC477139
0.8169	Intermediate Similarity	NPC53896
0.8162	Intermediate Similarity	NPC91478
0.8151	Intermediate Similarity	NPC203063
0.8148	Intermediate Similarity	NPC294361
0.8148	Intermediate Similarity	NPC236520
0.8143	Intermediate Similarity	NPC276238
0.8143	Intermediate Similarity	NPC303910
0.8143	Intermediate Similarity	NPC117899
0.8138	Intermediate Similarity	NPC87723
0.8138	Intermediate Similarity	NPC13715
0.8129	Intermediate Similarity	NPC471530
0.8125	Intermediate Similarity	NPC193358
0.8125	Intermediate Similarity	NPC194764
0.8125	Intermediate Similarity	NPC264112
0.8125	Intermediate Similarity	NPC65005
0.8112	Intermediate Similarity	NPC50924
0.8088	Intermediate Similarity	NPC120545
0.8071	Intermediate Similarity	NPC193203
0.8069	Intermediate Similarity	NPC53001
0.8067	Intermediate Similarity	NPC143685
0.8058	Intermediate Similarity	NPC71610
0.8058	Intermediate Similarity	NPC3224
0.8054	Intermediate Similarity	NPC309169
0.8054	Intermediate Similarity	NPC196941
0.8054	Intermediate Similarity	NPC79627
0.8045	Intermediate Similarity	NPC277394
0.8045	Intermediate Similarity	NPC61062
0.8045	Intermediate Similarity	NPC299252
0.8042	Intermediate Similarity	NPC327410
0.8042	Intermediate Similarity	NPC115458
0.8041	Intermediate Similarity	NPC193555
0.8041	Intermediate Similarity	NPC477873
0.8041	Intermediate Similarity	NPC469447
0.8039	Intermediate Similarity	NPC144283
0.8039	Intermediate Similarity	NPC35
0.8029	Intermediate Similarity	NPC139171
0.8029	Intermediate Similarity	NPC282577
0.8029	Intermediate Similarity	NPC86900
0.8028	Intermediate Similarity	NPC17083
0.8028	Intermediate Similarity	NPC291001
0.8028	Intermediate Similarity	NPC244699
0.8028	Intermediate Similarity	NPC18798
0.8028	Intermediate Similarity	NPC471851
0.8014	Intermediate Similarity	NPC206207
0.8014	Intermediate Similarity	NPC4214
0.8	Intermediate Similarity	NPC472308
0.8	Intermediate Similarity	NPC160777
0.8	Intermediate Similarity	NPC107672
0.8	Intermediate Similarity	NPC73416
0.7987	Intermediate Similarity	NPC239608
0.7987	Intermediate Similarity	NPC238629
0.7987	Intermediate Similarity	NPC46161
0.7986	Intermediate Similarity	NPC475088
0.7986	Intermediate Similarity	NPC293454
0.7986	Intermediate Similarity	NPC123506
0.7975	Intermediate Similarity	NPC471969
0.7973	Intermediate Similarity	NPC472410
0.7973	Intermediate Similarity	NPC84273
0.7972	Intermediate Similarity	NPC175738
0.7972	Intermediate Similarity	NPC135801
0.797	Intermediate Similarity	NPC322197
0.7956	Intermediate Similarity	NPC154696
0.7955	Intermediate Similarity	NPC234637
0.7955	Intermediate Similarity	NPC130591
0.7947	Intermediate Similarity	NPC476535
0.7945	Intermediate Similarity	NPC36868
0.7943	Intermediate Similarity	NPC3009
0.7943	Intermediate Similarity	NPC229894
0.7943	Intermediate Similarity	NPC48248
0.7933	Intermediate Similarity	NPC53520
0.7931	Intermediate Similarity	NPC477596
0.7931	Intermediate Similarity	NPC249272
0.7931	Intermediate Similarity	NPC283088
0.7929	Intermediate Similarity	NPC306765
0.7922	Intermediate Similarity	NPC124842
0.7922	Intermediate Similarity	NPC221249
0.7919	Intermediate Similarity	NPC11314
0.7917	Intermediate Similarity	NPC78307
0.7908	Intermediate Similarity	NPC474310
0.7908	Intermediate Similarity	NPC142654
0.7905	Intermediate Similarity	NPC181560
0.7905	Intermediate Similarity	NPC169452
0.7902	Intermediate Similarity	NPC469526
0.7902	Intermediate Similarity	NPC34070
0.7902	Intermediate Similarity	NPC243305
0.7899	Intermediate Similarity	NPC68167
0.7895	Intermediate Similarity	NPC476821
0.7891	Intermediate Similarity	NPC141368

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 NPC294330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	925
0.2-0.3	1440
0.3-0.4	2813
0.4-0.5	2188
0.5-0.6	1045
0.6-0.7	370
0.7-0.8	30
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
0.8219	Intermediate Similarity	NPD8166	Discontinued
0.7972	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD2932	Approved
0.781	Intermediate Similarity	NPD3019	Approved
0.773	Intermediate Similarity	NPD1470	Approved
0.7647	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3300	Phase 2
0.7571	Intermediate Similarity	NPD1201	Approved
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.7518	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3026	Approved
0.7376	Intermediate Similarity	NPD3023	Approved
0.7357	Intermediate Similarity	NPD3025	Approved
0.7357	Intermediate Similarity	NPD3024	Approved
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7273	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9494	Approved
0.7246	Intermediate Similarity	NPD7473	Discontinued
0.7244	Intermediate Similarity	NPD7390	Discontinued
0.7237	Intermediate Similarity	NPD5404	Approved
0.7237	Intermediate Similarity	NPD5405	Approved
0.7237	Intermediate Similarity	NPD5406	Approved
0.7237	Intermediate Similarity	NPD5408	Approved
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD2801	Approved
0.7143	Intermediate Similarity	NPD5736	Approved
0.7134	Intermediate Similarity	NPD1511	Approved
0.7125	Intermediate Similarity	NPD7458	Discontinued
0.7114	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD1934	Approved
0.7086	Intermediate Similarity	NPD230	Phase 1
0.7081	Intermediate Similarity	NPD7028	Phase 2
0.7078	Intermediate Similarity	NPD2344	Approved
0.7073	Intermediate Similarity	NPD3882	Suspended
0.7066	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7051	Intermediate Similarity	NPD4628	Phase 3
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1512	Approved
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7019	Intermediate Similarity	NPD3226	Approved
0.7013	Intermediate Similarity	NPD2935	Discontinued
0.7012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1164	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD5951	Approved
0.6993	Remote Similarity	NPD9268	Approved
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1471	Phase 3
0.6968	Remote Similarity	NPD2346	Discontinued
0.6966	Remote Similarity	NPD3092	Approved
0.6959	Remote Similarity	NPD2798	Approved
0.6951	Remote Similarity	NPD7819	Suspended
0.6944	Remote Similarity	NPD4059	Approved
0.6943	Remote Similarity	NPD7003	Approved
0.6932	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD3091	Approved
0.6903	Remote Similarity	NPD6099	Approved
0.6903	Remote Similarity	NPD6100	Approved
0.6899	Remote Similarity	NPD2309	Approved
0.6892	Remote Similarity	NPD3094	Phase 2
0.6879	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1755	Approved
0.6861	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7610	Discontinued
0.6842	Remote Similarity	NPD3020	Approved
0.6842	Remote Similarity	NPD8032	Phase 2
0.6839	Remote Similarity	NPD1510	Phase 2
0.6835	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6273	Approved
0.6828	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1876	Approved
0.6818	Remote Similarity	NPD6651	Approved
0.6818	Remote Similarity	NPD1607	Approved
0.6803	Remote Similarity	NPD4878	Approved
0.6802	Remote Similarity	NPD3818	Discontinued
0.6797	Remote Similarity	NPD1240	Approved
0.6797	Remote Similarity	NPD3620	Phase 2
0.6797	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2800	Approved
0.677	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4380	Phase 2
0.6766	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7236	Approved
0.6746	Remote Similarity	NPD5494	Approved
0.6743	Remote Similarity	NPD7685	Pre-registration
0.6743	Remote Similarity	NPD5027	Approved
0.6743	Remote Similarity	NPD5031	Approved
0.6743	Remote Similarity	NPD5029	Approved
0.6736	Remote Similarity	NPD5536	Phase 2
0.6733	Remote Similarity	NPD258	Approved
0.6733	Remote Similarity	NPD257	Approved
0.6726	Remote Similarity	NPD7075	Discontinued
0.6724	Remote Similarity	NPD7074	Phase 3
0.6712	Remote Similarity	NPD3095	Discontinued
0.6711	Remote Similarity	NPD1283	Approved
0.6711	Remote Similarity	NPD7095	Approved
0.6709	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3455	Phase 2
0.6706	Remote Similarity	NPD8127	Discontinued
0.6705	Remote Similarity	NPD36	Approved
0.6705	Remote Similarity	NPD5032	Approved
0.6705	Remote Similarity	NPD5034	Approved
0.6705	Remote Similarity	NPD5028	Approved
0.6705	Remote Similarity	NPD4955	Approved
0.6705	Remote Similarity	NPD4954	Approved
0.6705	Remote Similarity	NPD5026	Approved
0.669	Remote Similarity	NPD9545	Approved
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD3268	Approved
0.6648	Remote Similarity	NPD5030	Phase 2
0.6647	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1465	Phase 2
0.6645	Remote Similarity	NPD447	Suspended
0.6644	Remote Similarity	NPD1651	Approved
0.6629	Remote Similarity	NPD7472	Approved
0.6627	Remote Similarity	NPD7411	Suspended
0.6627	Remote Similarity	NPD6873	Phase 2
0.6625	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3750	Approved
0.6625	Remote Similarity	NPD4110	Phase 3
0.662	Remote Similarity	NPD7635	Approved
0.6617	Remote Similarity	NPD2859	Approved
0.6617	Remote Similarity	NPD2860	Approved
0.6607	Remote Similarity	NPD5977	Approved
0.6607	Remote Similarity	NPD5978	Approved
0.6607	Remote Similarity	NPD3817	Phase 2
0.6604	Remote Similarity	NPD1549	Phase 2
0.6601	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD826	Approved
0.6581	Remote Similarity	NPD825	Approved
0.6575	Remote Similarity	NPD6836	Approved
0.6575	Remote Similarity	NPD7009	Phase 2
0.6571	Remote Similarity	NPD74	Approved
0.6571	Remote Similarity	NPD9266	Approved
0.6571	Remote Similarity	NPD5844	Phase 1
0.6569	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1930	Approved
0.6569	Remote Similarity	NPD1929	Approved
0.6564	Remote Similarity	NPD2532	Approved
0.6564	Remote Similarity	NPD2534	Approved
0.6564	Remote Similarity	NPD2533	Approved
0.6556	Remote Similarity	NPD5038	Approved
0.6556	Remote Similarity	NPD5037	Approved
0.6554	Remote Similarity	NPD7251	Discontinued
0.6552	Remote Similarity	NPD9493	Approved
0.6548	Remote Similarity	NPD5761	Phase 2
0.6548	Remote Similarity	NPD5760	Phase 2
0.6545	Remote Similarity	NPD7239	Suspended
0.6541	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7266	Discontinued
0.6541	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2933	Approved
0.6541	Remote Similarity	NPD2934	Approved
0.6529	Remote Similarity	NPD3749	Approved
0.6528	Remote Similarity	NPD2629	Approved
0.6524	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7808	Phase 3
0.6516	Remote Similarity	NPD7961	Discontinued
0.6512	Remote Similarity	NPD6959	Discontinued
0.651	Remote Similarity	NPD1281	Approved
0.6503	Remote Similarity	NPD5968	Phase 3
0.65	Remote Similarity	NPD9264	Approved
0.65	Remote Similarity	NPD9267	Approved
0.65	Remote Similarity	NPD9263	Approved
0.65	Remote Similarity	NPD5036	Approved
0.6497	Remote Similarity	NPD6797	Phase 2
0.6497	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6234	Discontinued
0.6486	Remote Similarity	NPD1751	Approved
0.6481	Remote Similarity	NPD2354	Approved
0.648	Remote Similarity	NPD8313	Approved
0.648	Remote Similarity	NPD8312	Approved
0.6478	Remote Similarity	NPD2796	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