NPASS Compound

Structure

NPC75608 OpenBabel07101718222D 45 49 0 0 1 0 0 0 0 0999 V2000 2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1871 4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4743 5.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8270 5.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 33 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 12 1 0 0 0 0 10 23 2 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 34 1 0 0 0 0 16 27 1 0 0 0 0 16 35 1 0 0 0 0 17 21 1 0 0 0 0 17 37 1 0 0 0 0 18 21 1 0 0 0 0 18 38 1 0 0 0 0 19 39 1 0 0 0 0 20 1 1 1 0 0 0 20 22 1 0 0 0 0 22 35 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 36 1 1 0 0 0 25 19 1 6 0 0 0 25 29 1 0 0 0 0 25 44 1 0 0 0 0 26 34 1 6 0 0 0 26 36 1 0 0 0 0 27 36 1 6 0 0 0 27 40 1 0 0 0 0 28 33 1 0 0 0 0 28 45 1 1 0 0 0 29 30 1 0 0 0 0 29 41 1 1 0 0 0 30 31 1 0 0 0 0 30 42 1 6 0 0 0 31 32 1 0 0 0 0 31 43 1 1 0 0 0 32 44 1 0 0 0 0 32 45 1 6 0 0 0 34 35 1 6 0 0 0 35 5 1 1 0 0 0 36 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.42
Volume:	662.269
LogP:	3.929
LogD:	3.754
LogS:	-3.887
# Rotatable Bonds:	9
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	5.638
Fsp3:	0.889
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249
MDCK Permeability:	1.4537824426952284e-05
Pgp-inhibitor:	0.636
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.116
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.409

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	90.69506072998047%
Volume Distribution (VD):	0.749
Pgp-substrate:	3.902616024017334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	1.364
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.674
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC75608

Natural Product ID:	NPC75608
*Common Name:**	Jinfushanoside A
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(3S,8S,9R,10R,11R,13R,14S,17R)-11-hydroxy-17-[(2R)-7-hydroxy-6-(hydroxymethyl)hept-5-en-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	SIHQLSDQWIFIMC-GJUJOHLBSA-N
Standard InCHI:	InChI=1S/C36H60O9/c1-20(8-7-9-21(17-37)18-38)22-14-15-34(4)26-12-10-23-24(36(26,6)27(40)16-35(22,34)5)11-13-28(33(23,2)3)45-32-31(43)30(42)29(41)25(19-39)44-32/h9-10,20,22,24-32,37-43H,7-8,11-19H2,1-6H3/t20-,22-,24-,25-,26+,27-,28+,29-,30+,31-,32+,34+,35-,36+/m1/s1
SMILES:	OCC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)C[C@@H](O)[C@@]1([C@H]2CC=C2[C@H]1CC[C@@H](C2(C)C)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C)C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261682
PubChem CID:	90676077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO33474	hemsleya penxianensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717151]

☑ 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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	1.99	ug.mL-1	PMID[544158]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	3.84	ug.mL-1	PMID[544158]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.96	ug.mL-1	PMID[544158]

☑ 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 NPC75608 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	229
0.1-0.2	1676
0.2-0.3	5010
0.3-0.4	11729
0.4-0.5	10270
0.5-0.6	6094
0.6-0.7	4506
0.7-0.8	2461
0.8-0.85	505
0.85-0.9	170
0.9-0.95	39
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC472898
0.9694	High Similarity	NPC472899
0.9694	High Similarity	NPC472900
0.9691	High Similarity	NPC473198
0.9688	High Similarity	NPC470434
0.9592	High Similarity	NPC93352
0.9583	High Similarity	NPC469942
0.94	High Similarity	NPC231340
0.94	High Similarity	NPC33053
0.9394	High Similarity	NPC221562
0.9394	High Similarity	NPC187400
0.9394	High Similarity	NPC470885
0.9388	High Similarity	NPC136816
0.9381	High Similarity	NPC7341
0.9381	High Similarity	NPC473200
0.9381	High Similarity	NPC64348
0.9375	High Similarity	NPC243728
0.9375	High Similarity	NPC473890
0.9307	High Similarity	NPC472897
0.9307	High Similarity	NPC472896
0.93	High Similarity	NPC242748
0.9286	High Similarity	NPC4831
0.9286	High Similarity	NPC160734
0.9286	High Similarity	NPC47566
0.9286	High Similarity	NPC309425
0.9286	High Similarity	NPC129372
0.9286	High Similarity	NPC88000
0.9286	High Similarity	NPC472023
0.9278	High Similarity	NPC234287
0.9278	High Similarity	NPC158088
0.9278	High Similarity	NPC280825
0.9216	High Similarity	NPC250089
0.9216	High Similarity	NPC157530
0.9216	High Similarity	NPC472901
0.9216	High Similarity	NPC14630
0.9208	High Similarity	NPC190395
0.9192	High Similarity	NPC288694
0.9192	High Similarity	NPC159036
0.9192	High Similarity	NPC312553
0.9192	High Similarity	NPC272015
0.9184	High Similarity	NPC282669
0.9175	High Similarity	NPC240372
0.9135	High Similarity	NPC473567
0.9135	High Similarity	NPC216595
0.9126	High Similarity	NPC65155
0.9126	High Similarity	NPC141433
0.9126	High Similarity	NPC191439
0.9126	High Similarity	NPC170974
0.9126	High Similarity	NPC103627
0.9109	High Similarity	NPC309448
0.9109	High Similarity	NPC473923
0.9109	High Similarity	NPC473476
0.91	High Similarity	NPC155010
0.91	High Similarity	NPC286969
0.91	High Similarity	NPC16573
0.91	High Similarity	NPC213190
0.91	High Similarity	NPC120123
0.91	High Similarity	NPC473020
0.91	High Similarity	NPC114874
0.91	High Similarity	NPC472252
0.91	High Similarity	NPC16520
0.91	High Similarity	NPC131479
0.91	High Similarity	NPC162354
0.91	High Similarity	NPC211879
0.91	High Similarity	NPC8039
0.91	High Similarity	NPC157659
0.91	High Similarity	NPC31907
0.91	High Similarity	NPC245280
0.91	High Similarity	NPC189852
0.9091	High Similarity	NPC21568
0.9091	High Similarity	NPC285231
0.9091	High Similarity	NPC267510
0.9082	High Similarity	NPC476895
0.9072	High Similarity	NPC90583
0.9072	High Similarity	NPC207617
0.9062	High Similarity	NPC72817
0.9062	High Similarity	NPC477927
0.9057	High Similarity	NPC146652
0.9048	High Similarity	NPC307642
0.9038	High Similarity	NPC472987
0.9038	High Similarity	NPC473021
0.9029	High Similarity	NPC473328
0.9029	High Similarity	NPC28844
0.9029	High Similarity	NPC302057
0.9029	High Similarity	NPC473318
0.902	High Similarity	NPC473469
0.902	High Similarity	NPC226642
0.901	High Similarity	NPC165033
0.901	High Similarity	NPC470768
0.901	High Similarity	NPC273879
0.899	High Similarity	NPC91497
0.898	High Similarity	NPC476893
0.8969	High Similarity	NPC476894
0.8952	High Similarity	NPC231797
0.8952	High Similarity	NPC477050
0.8942	High Similarity	NPC472717
0.8932	High Similarity	NPC476541
0.8932	High Similarity	NPC235824
0.8932	High Similarity	NPC7213
0.8932	High Similarity	NPC476539
0.8932	High Similarity	NPC476540
0.8932	High Similarity	NPC476538
0.8922	High Similarity	NPC181845
0.8922	High Similarity	NPC160816
0.8922	High Similarity	NPC152584
0.8922	High Similarity	NPC26798
0.8922	High Similarity	NPC474569
0.8922	High Similarity	NPC208477
0.8922	High Similarity	NPC269627
0.8922	High Similarity	NPC473199
0.8922	High Similarity	NPC127801
0.8922	High Similarity	NPC69737
0.8922	High Similarity	NPC208594
0.8922	High Similarity	NPC194842
0.8911	High Similarity	NPC473124
0.8911	High Similarity	NPC473123
0.89	High Similarity	NPC476896
0.8889	High Similarity	NPC216260
0.8889	High Similarity	NPC5358
0.8878	High Similarity	NPC472989
0.8868	High Similarity	NPC51154
0.8866	High Similarity	NPC305160
0.8857	High Similarity	NPC472715
0.8857	High Similarity	NPC65034
0.8857	High Similarity	NPC114188
0.8857	High Similarity	NPC208189
0.8857	High Similarity	NPC197231
0.8857	High Similarity	NPC13190
0.8846	High Similarity	NPC475670
0.8846	High Similarity	NPC477026
0.8846	High Similarity	NPC306131
0.8846	High Similarity	NPC477027
0.8846	High Similarity	NPC70204
0.8835	High Similarity	NPC470432
0.8835	High Similarity	NPC476594
0.8835	High Similarity	NPC94272
0.8835	High Similarity	NPC63368
0.8835	High Similarity	NPC234160
0.8835	High Similarity	NPC283829
0.8835	High Similarity	NPC181467
0.8835	High Similarity	NPC230507
0.8835	High Similarity	NPC208650
0.8835	High Similarity	NPC113044
0.8835	High Similarity	NPC161676
0.8835	High Similarity	NPC14946
0.8835	High Similarity	NPC305423
0.8835	High Similarity	NPC14704
0.8824	High Similarity	NPC110656
0.8824	High Similarity	NPC203354
0.8824	High Similarity	NPC475365
0.8824	High Similarity	NPC473127
0.8824	High Similarity	NPC312774
0.8812	High Similarity	NPC154452
0.8788	High Similarity	NPC76486
0.8774	High Similarity	NPC19888
0.8774	High Similarity	NPC112274
0.8774	High Similarity	NPC472716
0.8762	High Similarity	NPC52241
0.8762	High Similarity	NPC475317
0.8762	High Similarity	NPC154856
0.875	High Similarity	NPC246124
0.875	High Similarity	NPC159005
0.875	High Similarity	NPC295980
0.875	High Similarity	NPC220427
0.875	High Similarity	NPC38217
0.875	High Similarity	NPC98696
0.875	High Similarity	NPC180183
0.875	High Similarity	NPC472988
0.875	High Similarity	NPC6931
0.8738	High Similarity	NPC165405
0.8738	High Similarity	NPC470763
0.8738	High Similarity	NPC470767
0.8725	High Similarity	NPC473129
0.8725	High Similarity	NPC475701
0.8725	High Similarity	NPC99627
0.8713	High Similarity	NPC263756
0.8713	High Similarity	NPC117714
0.8713	High Similarity	NPC121072
0.8713	High Similarity	NPC21064
0.8704	High Similarity	NPC207637
0.87	High Similarity	NPC477928
0.8692	High Similarity	NPC144068
0.8679	High Similarity	NPC476547
0.8679	High Similarity	NPC475247
0.8679	High Similarity	NPC263827
0.8679	High Similarity	NPC294129
0.8679	High Similarity	NPC250481
0.8679	High Similarity	NPC285410
0.8667	High Similarity	NPC248746
0.8667	High Similarity	NPC232054
0.8667	High Similarity	NPC244086
0.8667	High Similarity	NPC475550
0.8667	High Similarity	NPC42482
0.8667	High Similarity	NPC194207
0.8667	High Similarity	NPC476835
0.8667	High Similarity	NPC300557
0.8667	High Similarity	NPC296761
0.8667	High Similarity	NPC208383
0.8667	High Similarity	NPC43976
0.8667	High Similarity	NPC309278

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 NPC75608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1842
0.2-0.3	4094
0.3-0.4	1979
0.4-0.5	574
0.5-0.6	268
0.6-0.7	166
0.7-0.8	26
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD8033	Approved
0.823	Intermediate Similarity	NPD8377	Approved
0.823	Intermediate Similarity	NPD8294	Approved
0.8214	Intermediate Similarity	NPD7327	Approved
0.8214	Intermediate Similarity	NPD7328	Approved
0.8158	Intermediate Similarity	NPD8296	Approved
0.8158	Intermediate Similarity	NPD8335	Approved
0.8158	Intermediate Similarity	NPD8378	Approved
0.8158	Intermediate Similarity	NPD8380	Approved
0.8158	Intermediate Similarity	NPD8379	Approved
0.8142	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD7503	Approved
0.7963	Intermediate Similarity	NPD6412	Phase 2
0.7731	Intermediate Similarity	NPD7507	Approved
0.7658	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD8133	Approved
0.7541	Intermediate Similarity	NPD7319	Approved
0.7525	Intermediate Similarity	NPD7524	Approved
0.75	Intermediate Similarity	NPD8171	Discontinued
0.74	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7525	Registered
0.73	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD8328	Phase 3
0.7248	Intermediate Similarity	NPD7639	Approved
0.7248	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD8449	Approved
0.719	Intermediate Similarity	NPD6370	Approved
0.7188	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7339	Approved
0.7184	Intermediate Similarity	NPD7750	Discontinued
0.7184	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7736	Approved
0.7165	Intermediate Similarity	NPD8450	Suspended
0.7156	Intermediate Similarity	NPD7638	Approved
0.7107	Intermediate Similarity	NPD8517	Approved
0.7107	Intermediate Similarity	NPD8515	Approved
0.7107	Intermediate Similarity	NPD8516	Approved
0.7107	Intermediate Similarity	NPD8513	Phase 3
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.7071	Intermediate Similarity	NPD6929	Approved
0.7071	Intermediate Similarity	NPD7645	Phase 2
0.7059	Intermediate Similarity	NPD7115	Discovery
0.7025	Intermediate Similarity	NPD6054	Approved
0.7025	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD6931	Approved
0.6939	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5776	Phase 2
0.6869	Remote Similarity	NPD6925	Approved
0.6864	Remote Similarity	NPD8297	Approved
0.6864	Remote Similarity	NPD6882	Approved
0.6855	Remote Similarity	NPD6067	Discontinued
0.6852	Remote Similarity	NPD6399	Phase 3
0.6847	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6928	Phase 2
0.6832	Remote Similarity	NPD7514	Phase 3
0.6829	Remote Similarity	NPD6015	Approved
0.6829	Remote Similarity	NPD6016	Approved
0.68	Remote Similarity	NPD7492	Approved
0.68	Remote Similarity	NPD7145	Approved
0.6777	Remote Similarity	NPD6009	Approved
0.6774	Remote Similarity	NPD5988	Approved
0.6768	Remote Similarity	NPD6933	Approved
0.6765	Remote Similarity	NPD6902	Approved
0.6759	Remote Similarity	NPD7087	Discontinued
0.6759	Remote Similarity	NPD7637	Suspended
0.6748	Remote Similarity	NPD6319	Approved
0.6746	Remote Similarity	NPD6616	Approved
0.6731	Remote Similarity	NPD4786	Approved
0.6693	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6402	Approved
0.6638	Remote Similarity	NPD7128	Approved
0.6638	Remote Similarity	NPD5739	Approved
0.6638	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD6372	Approved
0.661	Remote Similarity	NPD6373	Approved
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8035	Phase 2
0.6606	Remote Similarity	NPD8034	Phase 2
0.6579	Remote Similarity	NPD4159	Approved
0.6579	Remote Similarity	NPD5344	Discontinued
0.6574	Remote Similarity	NPD5328	Approved
0.6566	Remote Similarity	NPD6924	Approved
0.6566	Remote Similarity	NPD6926	Approved
0.6547	Remote Similarity	NPD7625	Phase 1
0.6538	Remote Similarity	NPD3667	Approved
0.6535	Remote Similarity	NPD6932	Approved
0.6525	Remote Similarity	NPD6881	Approved
0.6525	Remote Similarity	NPD7320	Approved
0.6525	Remote Similarity	NPD6899	Approved
0.6522	Remote Similarity	NPD5211	Phase 2
0.6512	Remote Similarity	NPD6033	Approved
0.65	Remote Similarity	NPD6649	Approved
0.65	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD8264	Approved
0.65	Remote Similarity	NPD6650	Approved
0.6486	Remote Similarity	NPD7748	Approved
0.646	Remote Similarity	NPD4755	Approved
0.646	Remote Similarity	NPD7902	Approved
0.6455	Remote Similarity	NPD6079	Approved
0.6449	Remote Similarity	NPD3618	Phase 1
0.6442	Remote Similarity	NPD6898	Phase 1
0.6441	Remote Similarity	NPD5697	Approved
0.6441	Remote Similarity	NPD5701	Approved
0.6434	Remote Similarity	NPD8074	Phase 3
0.6422	Remote Similarity	NPD6051	Approved
0.6417	Remote Similarity	NPD4634	Approved
0.6417	Remote Similarity	NPD7102	Approved
0.6417	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7290	Approved
0.6417	Remote Similarity	NPD6883	Approved
0.6415	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5141	Approved
0.6408	Remote Similarity	NPD6683	Phase 2
0.6404	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4784	Approved
0.64	Remote Similarity	NPD4785	Approved
0.6396	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD7151	Approved
0.6364	Remote Similarity	NPD3168	Discontinued
0.6364	Remote Similarity	NPD4243	Approved
0.6364	Remote Similarity	NPD6869	Approved
0.6364	Remote Similarity	NPD7150	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD7152	Approved
0.6356	Remote Similarity	NPD6008	Approved
0.6356	Remote Similarity	NPD6640	Phase 3
0.6355	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5286	Approved
0.6348	Remote Similarity	NPD4696	Approved
0.6348	Remote Similarity	NPD5285	Approved
0.6348	Remote Similarity	NPD4700	Approved
0.6346	Remote Similarity	NPD7509	Discontinued
0.6346	Remote Similarity	NPD4748	Discontinued
0.6333	Remote Similarity	NPD6012	Approved
0.6333	Remote Similarity	NPD6014	Approved
0.6333	Remote Similarity	NPD6013	Approved
0.6328	Remote Similarity	NPD7604	Phase 2
0.6327	Remote Similarity	NPD6923	Approved
0.6327	Remote Similarity	NPD6922	Approved
0.6327	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7515	Phase 2
0.6299	Remote Similarity	NPD5983	Phase 2
0.6263	Remote Similarity	NPD7144	Approved
0.6263	Remote Similarity	NPD7143	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD5224	Approved
0.6239	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD4633	Approved
0.6238	Remote Similarity	NPD1811	Approved
0.6238	Remote Similarity	NPD1810	Approved
0.6231	Remote Similarity	NPD6336	Discontinued
0.623	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5222	Approved
0.6228	Remote Similarity	NPD4697	Phase 3
0.6228	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4768	Approved
0.6218	Remote Similarity	NPD4767	Approved
0.6216	Remote Similarity	NPD7838	Discovery
0.6216	Remote Similarity	NPD46	Approved
0.6216	Remote Similarity	NPD6698	Approved
0.6207	Remote Similarity	NPD6648	Approved
0.6195	Remote Similarity	NPD7900	Approved
0.6195	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5175	Approved
0.6186	Remote Similarity	NPD5174	Approved
0.6179	Remote Similarity	NPD6429	Approved
0.6179	Remote Similarity	NPD6053	Discontinued
0.6179	Remote Similarity	NPD6430	Approved
0.6174	Remote Similarity	NPD5173	Approved
0.6167	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7983	Approved
0.6154	Remote Similarity	NPD5223	Approved
0.614	Remote Similarity	NPD7991	Discontinued
0.6126	Remote Similarity	NPD4753	Phase 2
0.6124	Remote Similarity	NPD5126	Approved
0.6124	Remote Similarity	NPD5125	Phase 3
0.6116	Remote Similarity	NPD4730	Approved
0.6116	Remote Similarity	NPD4729	Approved
0.6111	Remote Similarity	NPD3666	Approved
0.6111	Remote Similarity	NPD3665	Phase 1
0.6111	Remote Similarity	NPD3133	Approved
0.6111	Remote Similarity	NPD3668	Phase 3
0.6106	Remote Similarity	NPD5779	Approved
0.6106	Remote Similarity	NPD5778	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