NPASS Compound

Structure

NPC271967 OpenBabel07101718242D 33 37 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 -4.8301 -0.6340 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 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 0 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 -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 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 28 1 0 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 30 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 31 1 6 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 6 0 0 0 24 27 1 1 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.34
Volume:	497.246
LogP:	4.411
LogD:	4.074
LogS:	-4.626
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	5.452
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:	-4.866
MDCK Permeability:	1.3914172996010166e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.807
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	92.0573501586914%
Volume Distribution (VD):	0.894
Pgp-substrate:	3.7153944969177246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.785

ADMET: Excretion

Clearance (CL):	9.778
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.708
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.854
Carcinogencity:	0.452
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC271967

Natural Product ID:	NPC271967
*Common Name:**	(+)-(3S,7S,8S,13R,14S,17R,18R,19R,21S)-25-Norfern-5(10),9-(11)-Diene-3,7,19,28-Tetraol
IUPAC Name:	(1R,3S,3aR,5aS,5bS,6S,9S,13aR,13bR)-3a-(hydroxymethyl)-5a,8,8,13a-tetramethyl-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:	XHVQNPUWDKXKRO-VCOJJVJASA-N
Standard InCHI:	InChI=1S/C29H46O4/c1-16(2)19-13-22(32)25-28(6)10-9-18-17-7-8-23(33)26(3,4)20(17)14-21(31)24(18)27(28,5)11-12-29(19,25)15-30/h9,16,19,21-25,30-33H,7-8,10-15H2,1-6H3/t19-,21-,22+,23-,24-,25+,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)(C)[C@H](CC5)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063149
PubChem CID:	60155758
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.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	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[546171]

☑ 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 NPC271967 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	167
0.1-0.2	1263
0.2-0.3	5784
0.3-0.4	16069
0.4-0.5	8267
0.5-0.6	6764
0.6-0.7	3582
0.7-0.8	727
0.8-0.85	61
0.85-0.9	9
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC2158
0.9643	High Similarity	NPC107189
0.9639	High Similarity	NPC470542
0.9167	High Similarity	NPC24277
0.9157	High Similarity	NPC124172
0.9146	High Similarity	NPC201852
0.9146	High Similarity	NPC470614
0.9146	High Similarity	NPC1272
0.8929	High Similarity	NPC209802
0.8916	High Similarity	NPC20853
0.8902	High Similarity	NPC26117
0.8851	High Similarity	NPC105495
0.881	High Similarity	NPC110778
0.8706	High Similarity	NPC475798
0.8706	High Similarity	NPC127606
0.8659	High Similarity	NPC275910
0.8659	High Similarity	NPC87604
0.8659	High Similarity	NPC186191
0.8659	High Similarity	NPC205455
0.8659	High Similarity	NPC477522
0.8588	High Similarity	NPC141941
0.8588	High Similarity	NPC477818
0.8588	High Similarity	NPC193870
0.8571	High Similarity	NPC127063
0.8554	High Similarity	NPC1319
0.8537	High Similarity	NPC214570
0.8506	High Similarity	NPC293287
0.8506	High Similarity	NPC201273
0.8506	High Similarity	NPC152808
0.8488	Intermediate Similarity	NPC238485
0.8471	Intermediate Similarity	NPC248886
0.8471	Intermediate Similarity	NPC202389
0.8452	Intermediate Similarity	NPC71535
0.8452	Intermediate Similarity	NPC78545
0.8434	Intermediate Similarity	NPC18603
0.8434	Intermediate Similarity	NPC318136
0.8434	Intermediate Similarity	NPC307965
0.8434	Intermediate Similarity	NPC76931
0.8415	Intermediate Similarity	NPC107059
0.8415	Intermediate Similarity	NPC73875
0.8415	Intermediate Similarity	NPC96319
0.8415	Intermediate Similarity	NPC202642
0.8415	Intermediate Similarity	NPC46160
0.8415	Intermediate Similarity	NPC321381
0.8415	Intermediate Similarity	NPC321016
0.8415	Intermediate Similarity	NPC470362
0.8372	Intermediate Similarity	NPC470384
0.8353	Intermediate Similarity	NPC209620
0.8353	Intermediate Similarity	NPC470383
0.8353	Intermediate Similarity	NPC23852
0.8353	Intermediate Similarity	NPC6707
0.8352	Intermediate Similarity	NPC310013
0.8333	Intermediate Similarity	NPC270511
0.8333	Intermediate Similarity	NPC245410
0.8333	Intermediate Similarity	NPC470390
0.8333	Intermediate Similarity	NPC192437
0.8315	Intermediate Similarity	NPC280556
0.8315	Intermediate Similarity	NPC474668
0.8315	Intermediate Similarity	NPC475664
0.8313	Intermediate Similarity	NPC155986
0.8313	Intermediate Similarity	NPC318495
0.8313	Intermediate Similarity	NPC198968
0.8295	Intermediate Similarity	NPC261266
0.8295	Intermediate Similarity	NPC139724
0.8295	Intermediate Similarity	NPC6391
0.8295	Intermediate Similarity	NPC6605
0.8293	Intermediate Similarity	NPC230301
0.8293	Intermediate Similarity	NPC257347
0.8293	Intermediate Similarity	NPC288035
0.8293	Intermediate Similarity	NPC28657
0.8293	Intermediate Similarity	NPC322353
0.8293	Intermediate Similarity	NPC285893
0.8293	Intermediate Similarity	NPC121744
0.8293	Intermediate Similarity	NPC22105
0.8293	Intermediate Similarity	NPC471468
0.8293	Intermediate Similarity	NPC134847
0.8293	Intermediate Similarity	NPC162742
0.8293	Intermediate Similarity	NPC136188
0.8293	Intermediate Similarity	NPC304309
0.8293	Intermediate Similarity	NPC141071
0.8293	Intermediate Similarity	NPC118508
0.8293	Intermediate Similarity	NPC471723
0.828	Intermediate Similarity	NPC253115
0.828	Intermediate Similarity	NPC304899
0.8276	Intermediate Similarity	NPC474493
0.8276	Intermediate Similarity	NPC231310
0.8272	Intermediate Similarity	NPC474140
0.8256	Intermediate Similarity	NPC50964
0.8256	Intermediate Similarity	NPC7988
0.8235	Intermediate Similarity	NPC322313
0.8235	Intermediate Similarity	NPC236237
0.8235	Intermediate Similarity	NPC102253
0.8214	Intermediate Similarity	NPC6978
0.8214	Intermediate Similarity	NPC244385
0.8214	Intermediate Similarity	NPC473943
0.8214	Intermediate Similarity	NPC477819
0.8214	Intermediate Similarity	NPC167037
0.8214	Intermediate Similarity	NPC477817
0.8214	Intermediate Similarity	NPC474216
0.8214	Intermediate Similarity	NPC138621
0.8214	Intermediate Similarity	NPC477514
0.8202	Intermediate Similarity	NPC186145
0.8202	Intermediate Similarity	NPC474657
0.8193	Intermediate Similarity	NPC129165
0.8193	Intermediate Similarity	NPC113733
0.8193	Intermediate Similarity	NPC189883
0.8193	Intermediate Similarity	NPC300324
0.8193	Intermediate Similarity	NPC240604
0.8193	Intermediate Similarity	NPC134330
0.8191	Intermediate Similarity	NPC190554
0.8182	Intermediate Similarity	NPC318390
0.8182	Intermediate Similarity	NPC474189
0.8182	Intermediate Similarity	NPC474349
0.8172	Intermediate Similarity	NPC45324
0.8172	Intermediate Similarity	NPC162001
0.8172	Intermediate Similarity	NPC222845
0.8161	Intermediate Similarity	NPC232023
0.8161	Intermediate Similarity	NPC237795
0.8161	Intermediate Similarity	NPC82538
0.8152	Intermediate Similarity	NPC98193
0.8152	Intermediate Similarity	NPC235126
0.8152	Intermediate Similarity	NPC242419
0.814	Intermediate Similarity	NPC474531
0.8132	Intermediate Similarity	NPC473956
0.8132	Intermediate Similarity	NPC14380
0.8132	Intermediate Similarity	NPC475751
0.8118	Intermediate Similarity	NPC47982
0.8118	Intermediate Similarity	NPC81306
0.8118	Intermediate Similarity	NPC109546
0.8118	Intermediate Similarity	NPC273410
0.8118	Intermediate Similarity	NPC328714
0.8118	Intermediate Similarity	NPC143182
0.8118	Intermediate Similarity	NPC84694
0.8118	Intermediate Similarity	NPC209430
0.8118	Intermediate Similarity	NPC30986
0.8118	Intermediate Similarity	NPC80530
0.8118	Intermediate Similarity	NPC472463
0.8118	Intermediate Similarity	NPC28862
0.8095	Intermediate Similarity	NPC34019
0.8095	Intermediate Similarity	NPC471798
0.809	Intermediate Similarity	NPC94462
0.8085	Intermediate Similarity	NPC173272
0.8072	Intermediate Similarity	NPC319090
0.8072	Intermediate Similarity	NPC328104
0.8068	Intermediate Similarity	NPC255882
0.8068	Intermediate Similarity	NPC478102
0.8065	Intermediate Similarity	NPC111015
0.8061	Intermediate Similarity	NPC477812
0.8049	Intermediate Similarity	NPC201373
0.8046	Intermediate Similarity	NPC30166
0.8046	Intermediate Similarity	NPC5985
0.8046	Intermediate Similarity	NPC87489
0.8046	Intermediate Similarity	NPC101462
0.8043	Intermediate Similarity	NPC41554
0.8043	Intermediate Similarity	NPC471453
0.8043	Intermediate Similarity	NPC97404
0.8041	Intermediate Similarity	NPC22634
0.8023	Intermediate Similarity	NPC209944
0.8023	Intermediate Similarity	NPC47149
0.8023	Intermediate Similarity	NPC164840
0.8023	Intermediate Similarity	NPC22403
0.8023	Intermediate Similarity	NPC236112
0.8023	Intermediate Similarity	NPC234193
0.8023	Intermediate Similarity	NPC241290
0.8022	Intermediate Similarity	NPC470361
0.8022	Intermediate Similarity	NPC109744
0.8021	Intermediate Similarity	NPC15390
0.8021	Intermediate Similarity	NPC208358
0.8	Intermediate Similarity	NPC72507
0.8	Intermediate Similarity	NPC475313
0.8	Intermediate Similarity	NPC475772
0.8	Intermediate Similarity	NPC285761
0.8	Intermediate Similarity	NPC475033
0.8	Intermediate Similarity	NPC475032
0.8	Intermediate Similarity	NPC177818
0.7979	Intermediate Similarity	NPC48330
0.7976	Intermediate Similarity	NPC237460
0.7976	Intermediate Similarity	NPC106432
0.7976	Intermediate Similarity	NPC274079
0.7976	Intermediate Similarity	NPC477925
0.7957	Intermediate Similarity	NPC472942
0.7957	Intermediate Similarity	NPC152897
0.7957	Intermediate Similarity	NPC66429
0.7955	Intermediate Similarity	NPC317458
0.7955	Intermediate Similarity	NPC113978
0.7955	Intermediate Similarity	NPC207013
0.7955	Intermediate Similarity	NPC474634
0.7952	Intermediate Similarity	NPC27395
0.7952	Intermediate Similarity	NPC329090
0.7938	Intermediate Similarity	NPC155974
0.7938	Intermediate Similarity	NPC474022
0.7935	Intermediate Similarity	NPC11216
0.7935	Intermediate Similarity	NPC3345
0.7935	Intermediate Similarity	NPC69622
0.7935	Intermediate Similarity	NPC329596
0.7935	Intermediate Similarity	NPC204188
0.7935	Intermediate Similarity	NPC295668
0.7935	Intermediate Similarity	NPC291484
0.7935	Intermediate Similarity	NPC80561
0.7931	Intermediate Similarity	NPC474731

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 NPC271967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1469
0.2-0.3	4401
0.3-0.4	2269
0.4-0.5	440
0.5-0.6	203
0.6-0.7	168
0.7-0.8	48
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8415	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6942	Approved
0.8293	Intermediate Similarity	NPD7339	Approved
0.8235	Intermediate Similarity	NPD7525	Registered
0.8023	Intermediate Similarity	NPD4748	Discontinued
0.8	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6926	Approved
0.7952	Intermediate Similarity	NPD6924	Approved
0.7907	Intermediate Similarity	NPD6929	Approved
0.7865	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6931	Approved
0.7816	Intermediate Similarity	NPD6930	Phase 2
0.7765	Intermediate Similarity	NPD6933	Approved
0.7753	Intermediate Similarity	NPD6695	Phase 3
0.7738	Intermediate Similarity	NPD4785	Approved
0.7738	Intermediate Similarity	NPD4784	Approved
0.7711	Intermediate Similarity	NPD7152	Approved
0.7711	Intermediate Similarity	NPD4243	Approved
0.7711	Intermediate Similarity	NPD7151	Approved
0.7711	Intermediate Similarity	NPD7150	Approved
0.7683	Intermediate Similarity	NPD6922	Approved
0.7683	Intermediate Similarity	NPD6923	Approved
0.7674	Intermediate Similarity	NPD6925	Approved
0.7674	Intermediate Similarity	NPD5776	Phase 2
0.7674	Intermediate Similarity	NPD6932	Approved
0.7667	Intermediate Similarity	NPD4786	Approved
0.7614	Intermediate Similarity	NPD7509	Discontinued
0.759	Intermediate Similarity	NPD7144	Approved
0.759	Intermediate Similarity	NPD7143	Approved
0.7586	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD6683	Phase 2
0.75	Intermediate Similarity	NPD7645	Phase 2
0.7444	Intermediate Similarity	NPD3667	Approved
0.7442	Intermediate Similarity	NPD8264	Approved
0.7419	Intermediate Similarity	NPD7750	Discontinued
0.7419	Intermediate Similarity	NPD7524	Approved
0.7416	Intermediate Similarity	NPD7514	Phase 3
0.7396	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD6893	Approved
0.7333	Intermediate Similarity	NPD6902	Approved
0.7312	Intermediate Similarity	NPD5279	Phase 3
0.7283	Intermediate Similarity	NPD3666	Approved
0.7283	Intermediate Similarity	NPD3665	Phase 1
0.7283	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD4755	Approved
0.7263	Intermediate Similarity	NPD5328	Approved
0.7241	Intermediate Similarity	NPD5275	Approved
0.7241	Intermediate Similarity	NPD4190	Phase 3
0.7222	Intermediate Similarity	NPD7332	Phase 2
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD6898	Phase 1
0.7129	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD4700	Approved
0.7129	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD4694	Approved
0.7128	Intermediate Similarity	NPD5280	Approved
0.7128	Intermediate Similarity	NPD3618	Phase 1
0.7113	Intermediate Similarity	NPD7087	Discontinued
0.7113	Intermediate Similarity	NPD6079	Approved
0.7113	Intermediate Similarity	NPD5284	Approved
0.7113	Intermediate Similarity	NPD5281	Approved
0.7111	Intermediate Similarity	NPD4195	Approved
0.7083	Intermediate Similarity	NPD4753	Phase 2
0.7059	Intermediate Similarity	NPD5223	Approved
0.703	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5226	Approved
0.699	Remote Similarity	NPD5225	Approved
0.699	Remote Similarity	NPD4633	Approved
0.699	Remote Similarity	NPD5224	Approved
0.699	Remote Similarity	NPD5211	Phase 2
0.6961	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6952	Remote Similarity	NPD7128	Approved
0.6952	Remote Similarity	NPD6675	Approved
0.6952	Remote Similarity	NPD6402	Approved
0.6952	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD4754	Approved
0.6915	Remote Similarity	NPD3668	Phase 3
0.6887	Remote Similarity	NPD6412	Phase 2
0.6882	Remote Similarity	NPD4221	Approved
0.6882	Remote Similarity	NPD4223	Phase 3
0.6857	Remote Similarity	NPD5141	Approved
0.6852	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5329	Approved
0.6832	Remote Similarity	NPD5222	Approved
0.6832	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5221	Approved
0.6822	Remote Similarity	NPD7320	Approved
0.6822	Remote Similarity	NPD6899	Approved
0.6822	Remote Similarity	NPD6881	Approved
0.6804	Remote Similarity	NPD4518	Approved
0.6792	Remote Similarity	NPD4768	Approved
0.6792	Remote Similarity	NPD4767	Approved
0.6771	Remote Similarity	NPD5690	Phase 2
0.6768	Remote Similarity	NPD7515	Phase 2
0.6768	Remote Similarity	NPD7637	Suspended
0.6765	Remote Similarity	NPD6084	Phase 2
0.6765	Remote Similarity	NPD6083	Phase 2
0.6765	Remote Similarity	NPD5173	Approved
0.6759	Remote Similarity	NPD6372	Approved
0.6759	Remote Similarity	NPD6373	Approved
0.6737	Remote Similarity	NPD4197	Approved
0.6735	Remote Similarity	NPD6051	Approved
0.6733	Remote Similarity	NPD5210	Approved
0.6733	Remote Similarity	NPD5695	Phase 3
0.6733	Remote Similarity	NPD4629	Approved
0.6729	Remote Similarity	NPD5701	Approved
0.6729	Remote Similarity	NPD5697	Approved
0.6697	Remote Similarity	NPD6883	Approved
0.6697	Remote Similarity	NPD7290	Approved
0.6697	Remote Similarity	NPD7102	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD4096	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6633	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4788	Approved
0.6606	Remote Similarity	NPD6012	Approved
0.6606	Remote Similarity	NPD6014	Approved
0.6606	Remote Similarity	NPD6013	Approved
0.66	Remote Similarity	NPD8034	Phase 2
0.66	Remote Similarity	NPD8035	Phase 2
0.66	Remote Similarity	NPD6411	Approved
0.66	Remote Similarity	NPD6050	Approved
0.6598	Remote Similarity	NPD7334	Approved
0.6598	Remote Similarity	NPD4690	Approved
0.6598	Remote Similarity	NPD4689	Approved
0.6598	Remote Similarity	NPD4693	Phase 3
0.6598	Remote Similarity	NPD7521	Approved
0.6598	Remote Similarity	NPD4688	Approved
0.6598	Remote Similarity	NPD5330	Approved
0.6598	Remote Similarity	NPD4138	Approved
0.6598	Remote Similarity	NPD6409	Approved
0.6598	Remote Similarity	NPD5205	Approved
0.6598	Remote Similarity	NPD7146	Approved
0.6598	Remote Similarity	NPD6684	Approved
0.6596	Remote Similarity	NPD4139	Approved
0.6596	Remote Similarity	NPD4692	Approved
0.6591	Remote Similarity	NPD4787	Phase 1
0.6579	Remote Similarity	NPD7328	Approved
0.6579	Remote Similarity	NPD7327	Approved
0.6577	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD6882	Approved
0.6552	Remote Similarity	NPD8033	Approved
0.6545	Remote Similarity	NPD5169	Approved
0.6545	Remote Similarity	NPD5250	Approved
0.6545	Remote Similarity	NPD5251	Approved
0.6545	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5247	Approved
0.6545	Remote Similarity	NPD5135	Approved
0.6545	Remote Similarity	NPD5249	Phase 3
0.6545	Remote Similarity	NPD5248	Approved
0.6535	Remote Similarity	NPD5133	Approved
0.6522	Remote Similarity	NPD7516	Approved
0.65	Remote Similarity	NPD5692	Phase 3
0.6491	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5216	Approved
0.6486	Remote Similarity	NPD5127	Approved
0.6486	Remote Similarity	NPD5217	Approved
0.6486	Remote Similarity	NPD5215	Approved
0.6477	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7748	Approved
0.6466	Remote Similarity	NPD6054	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6466	Remote Similarity	NPD6059	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6465	Remote Similarity	NPD6903	Approved
0.6465	Remote Similarity	NPD4723	Approved
0.6465	Remote Similarity	NPD4722	Approved
0.6442	Remote Similarity	NPD7902	Approved
0.6436	Remote Similarity	NPD5694	Approved
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8378	Approved
0.641	Remote Similarity	NPD8335	Approved
0.641	Remote Similarity	NPD8296	Approved
0.641	Remote Similarity	NPD8380	Approved
0.641	Remote Similarity	NPD8379	Approved
0.64	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6101	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