NPASS Compound

Structure

NPC2158 OpenBabel07101719152D 34 38 0 0 1 0 0 0 0 0999 V2000 1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.5981 -2.5000 0.0000 C 0 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 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 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 0.1910 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 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8301 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 2.5181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -0.7601 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 4 27 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 23 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 10 27 1 0 0 0 0 11 29 1 0 0 0 0 12 19 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 26 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 24 1 0 0 0 0 19 29 1 6 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 32 1 6 0 0 0 22 25 1 0 0 0 0 22 33 1 1 0 0 0 23 26 1 6 0 0 0 23 34 1 0 0 0 0 24 27 1 1 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 29 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.33
Volume:	506.036
LogP:	3.043
LogD:	3.204
LogS:	-4.248
# Rotatable Bonds:	3
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	5.598
Fsp3:	0.862
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:	-4.963
MDCK Permeability:	1.3664879588759504e-05
Pgp-inhibitor:	0.812
Pgp-substrate:	0.526
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.321

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	91.64090728759766%
Volume Distribution (VD):	0.737
Pgp-substrate:	4.215603828430176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.687

ADMET: Excretion

Clearance (CL):	6.426
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.432
Human Hepatotoxicity (H-HT):	0.386
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.913
Carcinogencity:	0.59
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC2158

Natural Product ID:	NPC2158
*Common Name:**	(+)-(3S,4R,7S,8S,13R,14S,17R,18R,19R,21S)-25-Norfern-5(10),9(11)-Diene-3,7,19,23,28-Pentaol
IUPAC Name:	(1R,3S,3aR,5aS,5bS,6S,8R,9S,13aR,13bR)-3a,8-bis(hydroxymethyl)-5a,8,13a-trimethyl-3-propan-2-yl-2,3,4,5,5b,6,7,9,10,11,13,13b-dodecahydro-1H-cyclopenta[a]chrysene-1,6,9-triol
Synonyms:
Standard InCHIKey:	NOVAZXBJXPYDOZ-LXMMOFSFSA-N
Standard InCHI:	InChI=1S/C29H46O5/c1-16(2)19-12-22(33)25-28(5)9-8-18-17-6-7-23(34)26(3,14-30)20(17)13-21(32)24(18)27(28,4)10-11-29(19,25)15-31/h8,16,19,21-25,30-34H,6-7,9-15H2,1-5H3/t19-,21-,22+,23-,24-,25+,26-,27-,28+,29+/m0/s1
SMILES:	CC(C)[C@@H]1C[C@H]([C@@H]2[C@@]3(C)CC=C4C5=C(C[C@@H]([C@H]4[C@]3(C)CC[C@@]12CO)O)[C@](C)(CO)[C@H](CC5)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063152
PubChem CID:	60155761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0004158] 1-hydroxysteroids

*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
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	6800.0	nM	PMID[524977]

☑ 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 NPC2158 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	175
0.1-0.2	1244
0.2-0.3	5573
0.3-0.4	15937
0.4-0.5	8385
0.5-0.6	6850
0.6-0.7	3776
0.7-0.8	703
0.8-0.85	43
0.85-0.9	7
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC271967
0.9529	High Similarity	NPC107189
0.9524	High Similarity	NPC470542
0.9059	High Similarity	NPC24277
0.9048	High Similarity	NPC124172
0.9036	High Similarity	NPC201852
0.9036	High Similarity	NPC470614
0.9036	High Similarity	NPC1272
0.8824	High Similarity	NPC209802
0.881	High Similarity	NPC20853
0.8795	High Similarity	NPC26117
0.875	High Similarity	NPC105495
0.8706	High Similarity	NPC110778
0.8621	High Similarity	NPC201273
0.8621	High Similarity	NPC293287
0.8621	High Similarity	NPC152808
0.8605	High Similarity	NPC127606
0.8605	High Similarity	NPC475798
0.8554	High Similarity	NPC477522
0.8554	High Similarity	NPC205455
0.8554	High Similarity	NPC186191
0.8554	High Similarity	NPC275910
0.8554	High Similarity	NPC87604
0.8488	Intermediate Similarity	NPC193870
0.8488	Intermediate Similarity	NPC477818
0.8488	Intermediate Similarity	NPC141941
0.8488	Intermediate Similarity	NPC470384
0.8478	Intermediate Similarity	NPC127063
0.8471	Intermediate Similarity	NPC470383
0.8462	Intermediate Similarity	NPC310013
0.8452	Intermediate Similarity	NPC1319
0.8444	Intermediate Similarity	NPC470390
0.8444	Intermediate Similarity	NPC270511
0.8444	Intermediate Similarity	NPC192437
0.8444	Intermediate Similarity	NPC245410
0.8434	Intermediate Similarity	NPC214570
0.8427	Intermediate Similarity	NPC475664
0.8409	Intermediate Similarity	NPC6605
0.8409	Intermediate Similarity	NPC6391
0.8391	Intermediate Similarity	NPC238485
0.8372	Intermediate Similarity	NPC248886
0.8372	Intermediate Similarity	NPC202389
0.8353	Intermediate Similarity	NPC71535
0.8353	Intermediate Similarity	NPC78545
0.8333	Intermediate Similarity	NPC76931
0.8333	Intermediate Similarity	NPC318136
0.8333	Intermediate Similarity	NPC307965
0.8333	Intermediate Similarity	NPC18603
0.8315	Intermediate Similarity	NPC186145
0.8315	Intermediate Similarity	NPC474657
0.8313	Intermediate Similarity	NPC96319
0.8313	Intermediate Similarity	NPC321016
0.8313	Intermediate Similarity	NPC107059
0.8313	Intermediate Similarity	NPC73875
0.8313	Intermediate Similarity	NPC202642
0.8313	Intermediate Similarity	NPC470362
0.8313	Intermediate Similarity	NPC46160
0.8313	Intermediate Similarity	NPC321381
0.8295	Intermediate Similarity	NPC474189
0.8295	Intermediate Similarity	NPC474349
0.8276	Intermediate Similarity	NPC232023
0.8276	Intermediate Similarity	NPC82538
0.8276	Intermediate Similarity	NPC237795
0.8261	Intermediate Similarity	NPC98193
0.8256	Intermediate Similarity	NPC209620
0.8256	Intermediate Similarity	NPC23852
0.8256	Intermediate Similarity	NPC6707
0.8242	Intermediate Similarity	NPC473956
0.8242	Intermediate Similarity	NPC475751
0.8242	Intermediate Similarity	NPC14380
0.8222	Intermediate Similarity	NPC280556
0.8222	Intermediate Similarity	NPC474668
0.8214	Intermediate Similarity	NPC318495
0.8214	Intermediate Similarity	NPC198968
0.8214	Intermediate Similarity	NPC155986
0.8202	Intermediate Similarity	NPC139724
0.8202	Intermediate Similarity	NPC261266
0.8193	Intermediate Similarity	NPC22105
0.8193	Intermediate Similarity	NPC230301
0.8193	Intermediate Similarity	NPC322353
0.8193	Intermediate Similarity	NPC471723
0.8193	Intermediate Similarity	NPC257347
0.8193	Intermediate Similarity	NPC288035
0.8193	Intermediate Similarity	NPC141071
0.8193	Intermediate Similarity	NPC136188
0.8193	Intermediate Similarity	NPC28657
0.8193	Intermediate Similarity	NPC285893
0.8193	Intermediate Similarity	NPC134847
0.8193	Intermediate Similarity	NPC121744
0.8193	Intermediate Similarity	NPC304309
0.8193	Intermediate Similarity	NPC471468
0.8193	Intermediate Similarity	NPC118508
0.8193	Intermediate Similarity	NPC162742
0.8191	Intermediate Similarity	NPC253115
0.8191	Intermediate Similarity	NPC304899
0.8182	Intermediate Similarity	NPC255882
0.8182	Intermediate Similarity	NPC231310
0.8182	Intermediate Similarity	NPC474493
0.8171	Intermediate Similarity	NPC474140
0.8161	Intermediate Similarity	NPC50964
0.8161	Intermediate Similarity	NPC30166
0.8161	Intermediate Similarity	NPC101462
0.8161	Intermediate Similarity	NPC7988
0.8152	Intermediate Similarity	NPC41554
0.8152	Intermediate Similarity	NPC97404
0.8144	Intermediate Similarity	NPC22634
0.814	Intermediate Similarity	NPC102253
0.814	Intermediate Similarity	NPC322313
0.814	Intermediate Similarity	NPC236237
0.8132	Intermediate Similarity	NPC470361
0.8132	Intermediate Similarity	NPC109744
0.8118	Intermediate Similarity	NPC477819
0.8118	Intermediate Similarity	NPC477817
0.8118	Intermediate Similarity	NPC477514
0.8118	Intermediate Similarity	NPC167037
0.8118	Intermediate Similarity	NPC473943
0.8118	Intermediate Similarity	NPC138621
0.8118	Intermediate Similarity	NPC474216
0.8118	Intermediate Similarity	NPC244385
0.8118	Intermediate Similarity	NPC6978
0.8111	Intermediate Similarity	NPC475313
0.8105	Intermediate Similarity	NPC177818
0.8105	Intermediate Similarity	NPC190554
0.8095	Intermediate Similarity	NPC189883
0.8095	Intermediate Similarity	NPC129165
0.8095	Intermediate Similarity	NPC113733
0.8095	Intermediate Similarity	NPC300324
0.8095	Intermediate Similarity	NPC240604
0.8095	Intermediate Similarity	NPC134330
0.809	Intermediate Similarity	NPC318390
0.8085	Intermediate Similarity	NPC222845
0.8085	Intermediate Similarity	NPC162001
0.8085	Intermediate Similarity	NPC45324
0.8068	Intermediate Similarity	NPC113978
0.8065	Intermediate Similarity	NPC235126
0.8065	Intermediate Similarity	NPC242419
0.8065	Intermediate Similarity	NPC472942
0.8046	Intermediate Similarity	NPC474531
0.8046	Intermediate Similarity	NPC320525
0.8043	Intermediate Similarity	NPC329596
0.8043	Intermediate Similarity	NPC204188
0.8043	Intermediate Similarity	NPC3345
0.8043	Intermediate Similarity	NPC291484
0.8043	Intermediate Similarity	NPC80561
0.8043	Intermediate Similarity	NPC11216
0.8041	Intermediate Similarity	NPC474022
0.8023	Intermediate Similarity	NPC209430
0.8023	Intermediate Similarity	NPC143182
0.8023	Intermediate Similarity	NPC109546
0.8023	Intermediate Similarity	NPC30986
0.8023	Intermediate Similarity	NPC80530
0.8023	Intermediate Similarity	NPC472463
0.8023	Intermediate Similarity	NPC84694
0.8023	Intermediate Similarity	NPC273410
0.8023	Intermediate Similarity	NPC28862
0.8023	Intermediate Similarity	NPC328714
0.8023	Intermediate Similarity	NPC47982
0.8023	Intermediate Similarity	NPC81306
0.8	Intermediate Similarity	NPC121981
0.8	Intermediate Similarity	NPC237344
0.8	Intermediate Similarity	NPC173272
0.8	Intermediate Similarity	NPC471798
0.8	Intermediate Similarity	NPC299068
0.8	Intermediate Similarity	NPC34019
0.8	Intermediate Similarity	NPC94462
0.798	Intermediate Similarity	NPC477812
0.7979	Intermediate Similarity	NPC111015
0.7978	Intermediate Similarity	NPC205845
0.7978	Intermediate Similarity	NPC185568
0.7978	Intermediate Similarity	NPC478102
0.7978	Intermediate Similarity	NPC256567
0.7976	Intermediate Similarity	NPC328104
0.7976	Intermediate Similarity	NPC319090
0.7957	Intermediate Similarity	NPC471453
0.7957	Intermediate Similarity	NPC210268
0.7955	Intermediate Similarity	NPC87489
0.7955	Intermediate Similarity	NPC5985
0.7952	Intermediate Similarity	NPC201373
0.7938	Intermediate Similarity	NPC208358
0.7938	Intermediate Similarity	NPC15390
0.7935	Intermediate Similarity	NPC101886
0.7931	Intermediate Similarity	NPC236112
0.7931	Intermediate Similarity	NPC324772
0.7931	Intermediate Similarity	NPC209944
0.7931	Intermediate Similarity	NPC475679
0.7931	Intermediate Similarity	NPC164840
0.7931	Intermediate Similarity	NPC47149
0.7931	Intermediate Similarity	NPC234193
0.7931	Intermediate Similarity	NPC241290
0.7931	Intermediate Similarity	NPC22403
0.7917	Intermediate Similarity	NPC475032
0.7917	Intermediate Similarity	NPC475033
0.7912	Intermediate Similarity	NPC475772
0.7912	Intermediate Similarity	NPC470620
0.7907	Intermediate Similarity	NPC285761
0.7907	Intermediate Similarity	NPC72507
0.7895	Intermediate Similarity	NPC48330
0.7889	Intermediate Similarity	NPC266511
0.7889	Intermediate Similarity	NPC470360
0.7882	Intermediate Similarity	NPC274079

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 NPC2158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1477
0.2-0.3	4376
0.3-0.4	2283
0.4-0.5	438
0.5-0.6	195
0.6-0.7	177
0.7-0.8	48
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6942	Approved
0.8193	Intermediate Similarity	NPD7339	Approved
0.814	Intermediate Similarity	NPD7525	Registered
0.8023	Intermediate Similarity	NPD6929	Approved
0.7978	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6931	Approved
0.7931	Intermediate Similarity	NPD6930	Phase 2
0.7931	Intermediate Similarity	NPD4748	Discontinued
0.7912	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6695	Phase 3
0.7857	Intermediate Similarity	NPD6924	Approved
0.7857	Intermediate Similarity	NPD6926	Approved
0.7791	Intermediate Similarity	NPD5776	Phase 2
0.7791	Intermediate Similarity	NPD6925	Approved
0.7791	Intermediate Similarity	NPD6932	Approved
0.7701	Intermediate Similarity	NPD7145	Approved
0.7674	Intermediate Similarity	NPD6933	Approved
0.7647	Intermediate Similarity	NPD4785	Approved
0.7647	Intermediate Similarity	NPD4784	Approved
0.7619	Intermediate Similarity	NPD7152	Approved
0.7619	Intermediate Similarity	NPD7151	Approved
0.7619	Intermediate Similarity	NPD4243	Approved
0.7619	Intermediate Similarity	NPD7150	Approved
0.7614	Intermediate Similarity	NPD7645	Phase 2
0.7614	Intermediate Similarity	NPD6683	Phase 2
0.759	Intermediate Similarity	NPD6922	Approved
0.759	Intermediate Similarity	NPD6923	Approved
0.7582	Intermediate Similarity	NPD4786	Approved
0.7528	Intermediate Similarity	NPD7514	Phase 3
0.7528	Intermediate Similarity	NPD7509	Discontinued
0.7527	Intermediate Similarity	NPD7750	Discontinued
0.7527	Intermediate Similarity	NPD7524	Approved
0.75	Intermediate Similarity	NPD6893	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.75	Intermediate Similarity	NPD7144	Approved
0.7444	Intermediate Similarity	NPD6902	Approved
0.7374	Intermediate Similarity	NPD4755	Approved
0.7363	Intermediate Similarity	NPD3667	Approved
0.7356	Intermediate Similarity	NPD8264	Approved
0.7333	Intermediate Similarity	NPD7332	Phase 2
0.732	Intermediate Similarity	NPD4202	Approved
0.7253	Intermediate Similarity	NPD6898	Phase 1
0.7234	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD5286	Approved
0.7228	Intermediate Similarity	NPD4696	Approved
0.7228	Intermediate Similarity	NPD5285	Approved
0.7228	Intermediate Similarity	NPD4700	Approved
0.7216	Intermediate Similarity	NPD7087	Discontinued
0.7204	Intermediate Similarity	NPD3666	Approved
0.7204	Intermediate Similarity	NPD3133	Approved
0.7204	Intermediate Similarity	NPD3665	Phase 1
0.7188	Intermediate Similarity	NPD4753	Phase 2
0.7188	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD5275	Approved
0.7159	Intermediate Similarity	NPD4190	Phase 3
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD5211	Phase 2
0.7087	Intermediate Similarity	NPD5226	Approved
0.7087	Intermediate Similarity	NPD5224	Approved
0.7087	Intermediate Similarity	NPD4633	Approved
0.7087	Intermediate Similarity	NPD5225	Approved
0.7053	Intermediate Similarity	NPD5280	Approved
0.7053	Intermediate Similarity	NPD4694	Approved
0.7053	Intermediate Similarity	NPD3618	Phase 1
0.7048	Intermediate Similarity	NPD6675	Approved
0.7048	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD7128	Approved
0.7048	Intermediate Similarity	NPD5739	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.7041	Intermediate Similarity	NPD5281	Approved
0.7041	Intermediate Similarity	NPD6079	Approved
0.7033	Intermediate Similarity	NPD4195	Approved
0.7019	Intermediate Similarity	NPD5175	Approved
0.7019	Intermediate Similarity	NPD5174	Approved
0.699	Remote Similarity	NPD5223	Approved
0.6981	Remote Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD7638	Approved
0.6952	Remote Similarity	NPD5141	Approved
0.6944	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7320	Approved
0.6916	Remote Similarity	NPD6899	Approved
0.6916	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6887	Remote Similarity	NPD4768	Approved
0.6887	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD6084	Phase 2
0.6863	Remote Similarity	NPD6083	Phase 2
0.6857	Remote Similarity	NPD4754	Approved
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6832	Remote Similarity	NPD4629	Approved
0.6832	Remote Similarity	NPD5695	Phase 3
0.6832	Remote Similarity	NPD5210	Approved
0.6822	Remote Similarity	NPD5701	Approved
0.6822	Remote Similarity	NPD5697	Approved
0.6809	Remote Similarity	NPD4223	Phase 3
0.6809	Remote Similarity	NPD4221	Approved
0.6789	Remote Similarity	NPD7102	Approved
0.6789	Remote Similarity	NPD7290	Approved
0.6789	Remote Similarity	NPD6883	Approved
0.6783	Remote Similarity	NPD7503	Approved
0.6771	Remote Similarity	NPD5329	Approved
0.6771	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7136	Phase 2
0.6765	Remote Similarity	NPD5221	Approved
0.6765	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5222	Approved
0.6759	Remote Similarity	NPD4730	Approved
0.6759	Remote Similarity	NPD4729	Approved
0.6759	Remote Similarity	NPD5128	Approved
0.6735	Remote Similarity	NPD4518	Approved
0.6727	Remote Similarity	NPD8130	Phase 1
0.6727	Remote Similarity	NPD6869	Approved
0.6727	Remote Similarity	NPD6649	Approved
0.6727	Remote Similarity	NPD6847	Approved
0.6727	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD6650	Approved
0.6701	Remote Similarity	NPD5690	Phase 2
0.67	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD5173	Approved
0.6697	Remote Similarity	NPD6013	Approved
0.6697	Remote Similarity	NPD6014	Approved
0.6697	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6638	Remote Similarity	NPD8033	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6609	Remote Similarity	NPD7516	Approved
0.6607	Remote Similarity	NPD4632	Approved
0.6606	Remote Similarity	NPD6011	Approved
0.66	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4096	Approved
0.6596	Remote Similarity	NPD6928	Phase 2
0.6591	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5215	Approved
0.6577	Remote Similarity	NPD5217	Approved
0.6577	Remote Similarity	NPD5216	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6566	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4788	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD8294	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6535	Remote Similarity	NPD8035	Phase 2
0.6535	Remote Similarity	NPD8034	Phase 2
0.6535	Remote Similarity	NPD6050	Approved
0.6531	Remote Similarity	NPD5205	Approved
0.6531	Remote Similarity	NPD4690	Approved
0.6531	Remote Similarity	NPD4138	Approved
0.6531	Remote Similarity	NPD7521	Approved
0.6531	Remote Similarity	NPD4689	Approved
0.6531	Remote Similarity	NPD6684	Approved
0.6531	Remote Similarity	NPD6409	Approved
0.6531	Remote Similarity	NPD7146	Approved
0.6531	Remote Similarity	NPD5330	Approved
0.6531	Remote Similarity	NPD4693	Phase 3
0.6531	Remote Similarity	NPD4688	Approved
0.6531	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD4692	Approved
0.6526	Remote Similarity	NPD4139	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6101	Approved
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8296	Approved
0.6496	Remote Similarity	NPD8380	Approved
0.6496	Remote Similarity	NPD8379	Approved
0.6486	Remote Similarity	NPD5169	Approved
0.6486	Remote Similarity	NPD5135	Approved
0.6486	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD5133	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6436	Remote Similarity	NPD5692	Phase 3
0.6435	Remote Similarity	NPD6009	Approved
0.6429	Remote Similarity	NPD5127	Approved
0.6421	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6319	Approved
0.6408	Remote Similarity	NPD7748	Approved
0.64	Remote Similarity	NPD4723	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