NPASS Compound

Structure

NPC475885 OpenBabel07101718182D 34 37 0 0 1 0 0 0 0 0999 V2000 -5.1507 -3.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2773 -3.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4188 -3.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 -3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 -3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 -3.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 -2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0299 -1.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 -0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 0.9740 0.0000 C 0 0 2 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 -0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 -1.4869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 22 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 23 1 0 0 0 0 17 25 1 0 0 0 0 17 27 1 1 0 0 0 19 13 1 6 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 27 1 6 0 0 0 21 24 1 0 0 0 0 21 27 1 1 0 0 0 22 30 2 0 0 0 0 22 34 1 0 0 0 0 23 31 2 0 0 0 0 24 26 1 0 0 0 0 24 28 1 6 0 0 0 25 28 1 6 0 0 0 25 34 1 0 0 0 0 26 28 1 0 0 0 0 27 32 1 1 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	495.541
LogP:	3.674
LogD:	2.911
LogS:	-4.499
# Rotatable Bonds:	7
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	5.405
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.756
MDCK Permeability:	1.5231514225888532e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.396
20% Bioavailability (F20%):	0.079
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.679
Plasma Protein Binding (PPB):	80.37899780273438%
Volume Distribution (VD):	0.843
Pgp-substrate:	12.18680477142334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.336
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	2.999
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.769
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.854
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.926
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.01
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: NPC475885

Natural Product ID:	NPC475885
*Common Name:**	RNSOPTPHJBVSTN-RWIQPIBWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RNSOPTPHJBVSTN-RWIQPIBWSA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-6-7-8-9-10-11-22(30)34-25-17(3)27(32)20-12-16(2)23(31)19(20)13-18(15-29)14-21(27)24-26(4,5)28(24,25)33/h8-12,14,17,19-21,24-25,29,32-33H,6-7,13,15H2,1-5H3/b9-8+,11-10-/t17-,19-,20-,21+,24-,25-,27+,28-/m1/s1
SMILES:	CCC/C=C/C=CC(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C(=O)[C@@H]3CC(=C[C@H]2[C@H]2[C@]1(O)C2(C)C)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517931
PubChem CID:	6443198
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[469552]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7612	Euphorbia tirucalli	Species	Euphorbiaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	>	100.0	ug	PMID[477608]

☑ 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 NPC475885 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	244
0.1-0.2	1273
0.2-0.3	3822
0.3-0.4	6309
0.4-0.5	12881
0.5-0.6	10251
0.6-0.7	6283
0.7-0.8	1398
0.8-0.85	117
0.85-0.9	51
0.9-0.95	42
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC156745
0.9909	High Similarity	NPC236918
0.982	High Similarity	NPC329080
0.982	High Similarity	NPC472759
0.964	High Similarity	NPC146280
0.964	High Similarity	NPC124676
0.9636	High Similarity	NPC154363
0.9636	High Similarity	NPC471127
0.9636	High Similarity	NPC234858
0.955	High Similarity	NPC10721
0.9545	High Similarity	NPC472400
0.9478	High Similarity	NPC145238
0.9455	High Similarity	NPC472757
0.9304	High Similarity	NPC257017
0.9304	High Similarity	NPC162009
0.9298	High Similarity	NPC471126
0.9298	High Similarity	NPC157252
0.9298	High Similarity	NPC471128
0.9298	High Similarity	NPC145182
0.9217	High Similarity	NPC52839
0.9204	High Similarity	NPC156252
0.913	High Similarity	NPC185876
0.913	High Similarity	NPC19336
0.9123	High Similarity	NPC472760
0.9123	High Similarity	NPC171905
0.9123	High Similarity	NPC471125
0.9123	High Similarity	NPC472397
0.9123	High Similarity	NPC472758
0.906	High Similarity	NPC472399
0.9043	High Similarity	NPC22628
0.9043	High Similarity	NPC471108
0.9043	High Similarity	NPC5989
0.9043	High Similarity	NPC5991
0.9043	High Similarity	NPC275696
0.9043	High Similarity	NPC255081
0.9043	High Similarity	NPC180640
0.8938	High Similarity	NPC71889
0.8889	High Similarity	NPC472401
0.887	High Similarity	NPC153651
0.886	High Similarity	NPC474872
0.8833	High Similarity	NPC471940
0.8814	High Similarity	NPC19464
0.8761	High Similarity	NPC174471
0.8761	High Similarity	NPC474871
0.8761	High Similarity	NPC475937
0.8761	High Similarity	NPC96739
0.8761	High Similarity	NPC260786
0.8761	High Similarity	NPC158523
0.876	High Similarity	NPC270109
0.876	High Similarity	NPC236999
0.875	High Similarity	NPC471939
0.8684	High Similarity	NPC151216
0.8684	High Similarity	NPC265499
0.8684	High Similarity	NPC221511
0.8684	High Similarity	NPC475391
0.8684	High Similarity	NPC17138
0.8684	High Similarity	NPC101825
0.8684	High Similarity	NPC170212
0.8684	High Similarity	NPC89227
0.8684	High Similarity	NPC215643
0.8673	High Similarity	NPC153036
0.8667	High Similarity	NPC473919
0.8667	High Similarity	NPC473709
0.8609	High Similarity	NPC474937
0.8595	High Similarity	NPC222307
0.8584	High Similarity	NPC163004
0.8583	High Similarity	NPC473802
0.8559	High Similarity	NPC472667
0.848	Intermediate Similarity	NPC476111
0.8448	Intermediate Similarity	NPC106395
0.8448	Intermediate Similarity	NPC469496
0.8448	Intermediate Similarity	NPC46269
0.8448	Intermediate Similarity	NPC469454
0.8448	Intermediate Similarity	NPC469463
0.8443	Intermediate Similarity	NPC293112
0.8421	Intermediate Similarity	NPC273433
0.8407	Intermediate Similarity	NPC187435
0.8407	Intermediate Similarity	NPC67321
0.8403	Intermediate Similarity	NPC470186
0.8376	Intermediate Similarity	NPC133677
0.8376	Intermediate Similarity	NPC138303
0.8376	Intermediate Similarity	NPC67290
0.8362	Intermediate Similarity	NPC138757
0.8362	Intermediate Similarity	NPC123855
0.8362	Intermediate Similarity	NPC76550
0.8333	Intermediate Similarity	NPC143755
0.8333	Intermediate Similarity	NPC475003
0.8319	Intermediate Similarity	NPC284707
0.8305	Intermediate Similarity	NPC179626
0.8291	Intermediate Similarity	NPC477091
0.8291	Intermediate Similarity	NPC471204
0.8279	Intermediate Similarity	NPC469789
0.8279	Intermediate Similarity	NPC11895
0.8276	Intermediate Similarity	NPC304180
0.8276	Intermediate Similarity	NPC179798
0.8268	Intermediate Similarity	NPC471137
0.8268	Intermediate Similarity	NPC182266
0.8268	Intermediate Similarity	NPC475500
0.8268	Intermediate Similarity	NPC475154
0.8268	Intermediate Similarity	NPC473548
0.8268	Intermediate Similarity	NPC471136
0.8268	Intermediate Similarity	NPC223356
0.8268	Intermediate Similarity	NPC100017
0.8264	Intermediate Similarity	NPC310511
0.8264	Intermediate Similarity	NPC67569
0.8254	Intermediate Similarity	NPC90814
0.8254	Intermediate Similarity	NPC189393
0.8235	Intermediate Similarity	NPC53396
0.8235	Intermediate Similarity	NPC98249
0.8235	Intermediate Similarity	NPC469684
0.822	Intermediate Similarity	NPC73314
0.8211	Intermediate Similarity	NPC81736
0.8211	Intermediate Similarity	NPC172154
0.8205	Intermediate Similarity	NPC472002
0.8197	Intermediate Similarity	NPC170538
0.8197	Intermediate Similarity	NPC23786
0.8197	Intermediate Similarity	NPC470265
0.819	Intermediate Similarity	NPC5103
0.819	Intermediate Similarity	NPC257240
0.8175	Intermediate Similarity	NPC475314
0.8175	Intermediate Similarity	NPC251564
0.8175	Intermediate Similarity	NPC475606
0.8175	Intermediate Similarity	NPC477189
0.8174	Intermediate Similarity	NPC306265
0.816	Intermediate Similarity	NPC470850
0.8151	Intermediate Similarity	NPC470793
0.8151	Intermediate Similarity	NPC471816
0.8151	Intermediate Similarity	NPC176840
0.8145	Intermediate Similarity	NPC473635
0.8142	Intermediate Similarity	NPC23584
0.814	Intermediate Similarity	NPC68282
0.8136	Intermediate Similarity	NPC56448
0.8134	Intermediate Similarity	NPC140021
0.813	Intermediate Similarity	NPC473979
0.812	Intermediate Similarity	NPC474846
0.812	Intermediate Similarity	NPC469655
0.812	Intermediate Similarity	NPC188738
0.812	Intermediate Similarity	NPC470076
0.812	Intermediate Similarity	NPC469656
0.811	Intermediate Similarity	NPC475139
0.811	Intermediate Similarity	NPC180902
0.811	Intermediate Similarity	NPC473485
0.811	Intermediate Similarity	NPC474508
0.8103	Intermediate Similarity	NPC47951
0.8099	Intermediate Similarity	NPC475041
0.8095	Intermediate Similarity	NPC470851
0.8095	Intermediate Similarity	NPC104382
0.8095	Intermediate Similarity	NPC231529
0.8087	Intermediate Similarity	NPC143609
0.8083	Intermediate Similarity	NPC474518
0.8083	Intermediate Similarity	NPC312824
0.8083	Intermediate Similarity	NPC475323
0.8083	Intermediate Similarity	NPC470493
0.8083	Intermediate Similarity	NPC284068
0.8083	Intermediate Similarity	NPC23046
0.8083	Intermediate Similarity	NPC183580
0.8065	Intermediate Similarity	NPC8369
0.8053	Intermediate Similarity	NPC478156
0.8053	Intermediate Similarity	NPC11956
0.8053	Intermediate Similarity	NPC476081
0.8051	Intermediate Similarity	NPC476801
0.8051	Intermediate Similarity	NPC152117
0.8051	Intermediate Similarity	NPC234042
0.8051	Intermediate Similarity	NPC470063
0.8051	Intermediate Similarity	NPC236217
0.8051	Intermediate Similarity	NPC269530
0.8034	Intermediate Similarity	NPC253906
0.8034	Intermediate Similarity	NPC477103
0.8033	Intermediate Similarity	NPC4548
0.8033	Intermediate Similarity	NPC268530
0.8033	Intermediate Similarity	NPC154491
0.8033	Intermediate Similarity	NPC48692
0.8018	Intermediate Similarity	NPC120446
0.8017	Intermediate Similarity	NPC478205
0.8017	Intermediate Similarity	NPC478206
0.8017	Intermediate Similarity	NPC108581
0.8017	Intermediate Similarity	NPC50774
0.8017	Intermediate Similarity	NPC469916
0.8017	Intermediate Similarity	NPC472439
0.8017	Intermediate Similarity	NPC102843
0.8017	Intermediate Similarity	NPC709
0.8017	Intermediate Similarity	NPC186525
0.8	Intermediate Similarity	NPC470075
0.8	Intermediate Similarity	NPC111952
0.8	Intermediate Similarity	NPC477125
0.8	Intermediate Similarity	NPC34768
0.8	Intermediate Similarity	NPC243902
0.8	Intermediate Similarity	NPC64318
0.7984	Intermediate Similarity	NPC469352
0.7983	Intermediate Similarity	NPC477126
0.7983	Intermediate Similarity	NPC475966
0.7983	Intermediate Similarity	NPC474271
0.7983	Intermediate Similarity	NPC25909
0.7982	Intermediate Similarity	NPC99266
0.7982	Intermediate Similarity	NPC61442
0.7967	Intermediate Similarity	NPC159456
0.7967	Intermediate Similarity	NPC4021
0.7967	Intermediate Similarity	NPC46570
0.7966	Intermediate Similarity	NPC132790
0.7966	Intermediate Similarity	NPC97939

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 NPC475885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1528
0.2-0.3	3484
0.3-0.4	2463
0.4-0.5	939
0.5-0.6	372
0.6-0.7	142
0.7-0.8	9
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD6371	Approved
0.7965	Intermediate Similarity	NPD5344	Discontinued
0.7934	Intermediate Similarity	NPD7115	Discovery
0.7876	Intermediate Similarity	NPD6648	Approved
0.7797	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6686	Approved
0.7265	Intermediate Similarity	NPD7639	Approved
0.7265	Intermediate Similarity	NPD7640	Approved
0.7258	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD6319	Approved
0.7179	Intermediate Similarity	NPD7638	Approved
0.7177	Intermediate Similarity	NPD8297	Approved
0.7176	Intermediate Similarity	NPD7507	Approved
0.7168	Intermediate Similarity	NPD6698	Approved
0.7168	Intermediate Similarity	NPD46	Approved
0.7168	Intermediate Similarity	NPD7838	Discovery
0.7154	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD7319	Approved
0.7131	Intermediate Similarity	NPD6899	Approved
0.7131	Intermediate Similarity	NPD6881	Approved
0.7109	Intermediate Similarity	NPD7516	Approved
0.7097	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD6649	Approved
0.7069	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5697	Approved
0.7031	Intermediate Similarity	NPD7327	Approved
0.7031	Intermediate Similarity	NPD7328	Approved
0.7016	Intermediate Similarity	NPD7290	Approved
0.7016	Intermediate Similarity	NPD7102	Approved
0.7016	Intermediate Similarity	NPD6883	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.7	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.697	Remote Similarity	NPD7492	Approved
0.6967	Remote Similarity	NPD5739	Approved
0.6967	Remote Similarity	NPD6008	Approved
0.6967	Remote Similarity	NPD7128	Approved
0.6967	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6402	Approved
0.696	Remote Similarity	NPD8130	Phase 1
0.696	Remote Similarity	NPD6869	Approved
0.696	Remote Similarity	NPD6847	Approved
0.696	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD7983	Approved
0.6953	Remote Similarity	NPD6009	Approved
0.6935	Remote Similarity	NPD6012	Approved
0.6935	Remote Similarity	NPD6373	Approved
0.6935	Remote Similarity	NPD6372	Approved
0.6935	Remote Similarity	NPD6013	Approved
0.6935	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6905	Remote Similarity	NPD6053	Discontinued
0.6905	Remote Similarity	NPD6882	Approved
0.6897	Remote Similarity	NPD5779	Approved
0.6897	Remote Similarity	NPD5778	Approved
0.6891	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5983	Phase 2
0.687	Remote Similarity	NPD6921	Approved
0.6866	Remote Similarity	NPD7078	Approved
0.686	Remote Similarity	NPD5211	Phase 2
0.6855	Remote Similarity	NPD7320	Approved
0.6855	Remote Similarity	NPD6011	Approved
0.6818	Remote Similarity	NPD6370	Approved
0.6815	Remote Similarity	NPD7736	Approved
0.681	Remote Similarity	NPD7637	Suspended
0.6791	Remote Similarity	NPD6336	Discontinued
0.6788	Remote Similarity	NPD7260	Phase 2
0.6774	Remote Similarity	NPD5701	Approved
0.6754	Remote Similarity	NPD7524	Approved
0.6752	Remote Similarity	NPD6399	Phase 3
0.6748	Remote Similarity	NPD5141	Approved
0.6746	Remote Similarity	NPD4634	Approved
0.6742	Remote Similarity	NPD8380	Approved
0.6742	Remote Similarity	NPD8335	Approved
0.6742	Remote Similarity	NPD6016	Approved
0.6742	Remote Similarity	NPD8379	Approved
0.6742	Remote Similarity	NPD8296	Approved
0.6742	Remote Similarity	NPD8033	Approved
0.6742	Remote Similarity	NPD6015	Approved
0.6742	Remote Similarity	NPD8378	Approved
0.6741	Remote Similarity	NPD8074	Phase 3
0.6726	Remote Similarity	NPD1694	Approved
0.6726	Remote Similarity	NPD1696	Phase 3
0.6724	Remote Similarity	NPD5785	Approved
0.6721	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD5286	Approved
0.6694	Remote Similarity	NPD5285	Approved
0.6694	Remote Similarity	NPD4696	Approved
0.6692	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.6642	Remote Similarity	NPD8328	Phase 3
0.664	Remote Similarity	NPD6412	Phase 2
0.6638	Remote Similarity	NPD1695	Approved
0.6618	Remote Similarity	NPD8293	Discontinued
0.6591	Remote Similarity	NPD7100	Approved
0.6591	Remote Similarity	NPD7101	Approved
0.6589	Remote Similarity	NPD8133	Approved
0.6585	Remote Similarity	NPD5224	Approved
0.6585	Remote Similarity	NPD5226	Approved
0.6585	Remote Similarity	NPD4633	Approved
0.6585	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7748	Approved
0.6555	Remote Similarity	NPD5282	Discontinued
0.6532	Remote Similarity	NPD5174	Approved
0.6532	Remote Similarity	NPD5175	Approved
0.6529	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD6083	Phase 2
0.6529	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD6411	Approved
0.6525	Remote Similarity	NPD7515	Phase 2
0.6525	Remote Similarity	NPD5284	Approved
0.6525	Remote Similarity	NPD5281	Approved
0.6515	Remote Similarity	NPD6335	Approved
0.6504	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5328	Approved
0.6491	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6274	Approved
0.646	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5209	Approved
0.6446	Remote Similarity	NPD5222	Approved
0.6446	Remote Similarity	NPD5221	Approved
0.6446	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6317	Approved
0.6435	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4700	Approved
0.6417	Remote Similarity	NPD7900	Approved
0.6417	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6695	Phase 3
0.6393	Remote Similarity	NPD5173	Approved
0.6391	Remote Similarity	NPD6313	Approved
0.6391	Remote Similarity	NPD6314	Approved
0.6383	Remote Similarity	NPD6845	Suspended
0.6379	Remote Similarity	NPD3618	Phase 1
0.637	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6356	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6101	Approved
0.6341	Remote Similarity	NPD5696	Approved
0.6333	Remote Similarity	NPD4202	Approved
0.6328	Remote Similarity	NPD4730	Approved
0.6328	Remote Similarity	NPD4729	Approved
0.6325	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4697	Phase 3
0.6293	Remote Similarity	NPD5363	Approved
0.6283	Remote Similarity	NPD7332	Phase 2
0.6261	Remote Similarity	NPD7154	Phase 3
0.6261	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.6231	Remote Similarity	NPD5250	Approved
0.6231	Remote Similarity	NPD5247	Approved
0.6231	Remote Similarity	NPD5251	Approved
0.6231	Remote Similarity	NPD5249	Phase 3
0.6231	Remote Similarity	NPD5248	Approved
0.623	Remote Similarity	NPD4629	Approved
0.623	Remote Similarity	NPD5210	Approved
0.6228	Remote Similarity	NPD6902	Approved
0.6214	Remote Similarity	NPD6033	Approved
0.6207	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4786	Approved
0.6202	Remote Similarity	NPD5128	Approved
0.6187	Remote Similarity	NPD8273	Phase 1
0.6186	Remote Similarity	NPD7750	Discontinued
0.6184	Remote Similarity	NPD7236	Approved
0.6183	Remote Similarity	NPD5215	Approved
0.6183	Remote Similarity	NPD5217	Approved
0.6183	Remote Similarity	NPD5216	Approved
0.6179	Remote Similarity	NPD7839	Suspended
0.6176	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4767	Approved
0.6172	Remote Similarity	NPD4768	Approved
0.6167	Remote Similarity	NPD5207	Approved
0.6159	Remote Similarity	NPD7830	Approved
0.6159	Remote Similarity	NPD7829	Approved
0.6159	Remote Similarity	NPD7642	Approved
0.6148	Remote Similarity	NPD6001	Approved
0.6148	Remote Similarity	NPD7641	Discontinued
0.6142	Remote Similarity	NPD4754	Approved
0.614	Remote Similarity	NPD6930	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