NPASS Compound

Structure

NPC16350 OpenBabel07101718322D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.8234 -3.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 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 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 -1.1977 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 -1.2024 1.0827 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 2.5981 -3.5000 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 -0.2079 0.9781 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 -3.5144 -2.8920 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 -0.9898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 -2.6840 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8671 -3.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 -1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 2 1 1 0 0 0 19 20 1 0 0 0 0 20 29 1 1 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 19 1 1 0 0 0 23 33 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 31 1 6 0 0 0 26 32 1 6 0 0 0 26 33 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	5.767
LogD:	4.768
LogS:	-5.731
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	5.068
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.941
MDCK Permeability:	1.4783033293497283e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.858

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	93.6361312866211%
Volume Distribution (VD):	1.227
Pgp-substrate:	1.2848851680755615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.545
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.369
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.69
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.779

ADMET: Excretion

Clearance (CL):	5.802
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.752
Skin Sensitization:	0.908
Carcinogencity:	0.019
Eye Corrosion:	0.107
Eye Irritation:	0.445
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC16350

Natural Product ID:	NPC16350
*Common Name:**	3-Epi-Astrapteridiol
IUPAC Name:	(2S,3S,6S)-6-[(1S)-1-[(3R,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-methyloxan-2-ol
Synonyms:	3-Epi-Astrapteridiol
Standard InCHIKey:	DRTROQLYCJSMQX-GSULAHQPSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-18-8-10-23(33-26(18)32)19(2)20-12-16-30(7)22-9-11-24-27(3,4)25(31)14-15-28(24,5)21(22)13-17-29(20,30)6/h18-20,23-26,31-32H,8-17H2,1-7H3/t18-,19-,20+,23-,24-,25+,26-,28+,29+,30-/m0/s1
SMILES:	C[C@H]1CC[C@@H]([C@@H](C)[C@H]2CC[C@@]3(C)C4=C(CC[C@]23C)[C@@]2(C)CC[C@H](C(C)(C)[C@@H]2CC4)O)O[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460495
PubChem CID:	25178598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO22791	Astraeus pteridis	Species	Astraeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19067555]
NPO22791	Astraeus pteridis	Species	Astraeaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	34.0	ug.mL-1	PMID[508850]

☑ 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 NPC16350 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	197
0.1-0.2	1893
0.2-0.3	7634
0.3-0.4	15259
0.4-0.5	6997
0.5-0.6	4739
0.6-0.7	4874
0.7-0.8	1064
0.8-0.85	37
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC308041
0.8736	High Similarity	NPC219495
0.8481	Intermediate Similarity	NPC201373
0.8395	Intermediate Similarity	NPC73875
0.8333	Intermediate Similarity	NPC470923
0.8293	Intermediate Similarity	NPC214570
0.828	Intermediate Similarity	NPC234287
0.828	Intermediate Similarity	NPC275865
0.828	Intermediate Similarity	NPC280825
0.8272	Intermediate Similarity	NPC121744
0.8272	Intermediate Similarity	NPC118508
0.8272	Intermediate Similarity	NPC322353
0.8235	Intermediate Similarity	NPC7988
0.8222	Intermediate Similarity	NPC94127
0.8193	Intermediate Similarity	NPC275910
0.8191	Intermediate Similarity	NPC7341
0.8191	Intermediate Similarity	NPC473200
0.8172	Intermediate Similarity	NPC243728
0.8172	Intermediate Similarity	NPC473890
0.8171	Intermediate Similarity	NPC46160
0.8171	Intermediate Similarity	NPC202642
0.8152	Intermediate Similarity	NPC476894
0.814	Intermediate Similarity	NPC132635
0.8132	Intermediate Similarity	NPC242419
0.8132	Intermediate Similarity	NPC235126
0.8111	Intermediate Similarity	NPC20388
0.8105	Intermediate Similarity	NPC129372
0.8105	Intermediate Similarity	NPC4831
0.8105	Intermediate Similarity	NPC472023
0.8105	Intermediate Similarity	NPC309425
0.8105	Intermediate Similarity	NPC160734
0.8105	Intermediate Similarity	NPC47566
0.8105	Intermediate Similarity	NPC88000
0.8095	Intermediate Similarity	NPC155924
0.8085	Intermediate Similarity	NPC216260
0.8085	Intermediate Similarity	NPC158088
0.8085	Intermediate Similarity	NPC5358
0.8065	Intermediate Similarity	NPC207617
0.8046	Intermediate Similarity	NPC209802
0.8043	Intermediate Similarity	NPC305160
0.8043	Intermediate Similarity	NPC189513
0.8041	Intermediate Similarity	NPC221562
0.8041	Intermediate Similarity	NPC187400
0.8041	Intermediate Similarity	NPC470885
0.8041	Intermediate Similarity	NPC75608
0.8023	Intermediate Similarity	NPC20853
0.8023	Intermediate Similarity	NPC248886
0.8021	Intermediate Similarity	NPC159036
0.8021	Intermediate Similarity	NPC22634
0.8021	Intermediate Similarity	NPC288694
0.8021	Intermediate Similarity	NPC136816
0.8021	Intermediate Similarity	NPC312553
0.8	Intermediate Similarity	NPC22403
0.8	Intermediate Similarity	NPC282669
0.8	Intermediate Similarity	NPC324598
0.7979	Intermediate Similarity	NPC177818
0.7979	Intermediate Similarity	NPC476893
0.7976	Intermediate Similarity	NPC87604
0.7976	Intermediate Similarity	NPC186191
0.7976	Intermediate Similarity	NPC205455
0.7959	Intermediate Similarity	NPC242748
0.7957	Intermediate Similarity	NPC135224
0.7957	Intermediate Similarity	NPC477970
0.7957	Intermediate Similarity	NPC477969
0.7957	Intermediate Similarity	NPC100892
0.7952	Intermediate Similarity	NPC470362
0.7952	Intermediate Similarity	NPC189883
0.7938	Intermediate Similarity	NPC213190
0.7938	Intermediate Similarity	NPC31907
0.7938	Intermediate Similarity	NPC473020
0.7938	Intermediate Similarity	NPC472252
0.7938	Intermediate Similarity	NPC131479
0.7938	Intermediate Similarity	NPC473198
0.7938	Intermediate Similarity	NPC155010
0.7938	Intermediate Similarity	NPC157659
0.7938	Intermediate Similarity	NPC16520
0.7938	Intermediate Similarity	NPC16573
0.7938	Intermediate Similarity	NPC286969
0.7938	Intermediate Similarity	NPC245280
0.7938	Intermediate Similarity	NPC189852
0.7938	Intermediate Similarity	NPC8039
0.7938	Intermediate Similarity	NPC211879
0.7938	Intermediate Similarity	NPC120123
0.7938	Intermediate Similarity	NPC114874
0.7935	Intermediate Similarity	NPC27918
0.7917	Intermediate Similarity	NPC470434
0.7917	Intermediate Similarity	NPC267510
0.7917	Intermediate Similarity	NPC474022
0.7912	Intermediate Similarity	NPC192437
0.7912	Intermediate Similarity	NPC470390
0.7912	Intermediate Similarity	NPC245410
0.7912	Intermediate Similarity	NPC270511
0.7907	Intermediate Similarity	NPC470383
0.7907	Intermediate Similarity	NPC6707
0.79	Intermediate Similarity	NPC477070
0.79	Intermediate Similarity	NPC477069
0.7895	Intermediate Similarity	NPC476895
0.7889	Intermediate Similarity	NPC470542
0.7882	Intermediate Similarity	NPC1319
0.7879	Intermediate Similarity	NPC190395
0.7872	Intermediate Similarity	NPC472989
0.7865	Intermediate Similarity	NPC474970
0.7865	Intermediate Similarity	NPC24277
0.7857	Intermediate Similarity	NPC93352
0.7857	Intermediate Similarity	NPC165033
0.7857	Intermediate Similarity	NPC202540
0.7857	Intermediate Similarity	NPC273879
0.7849	Intermediate Similarity	NPC477927
0.7849	Intermediate Similarity	NPC474922
0.7849	Intermediate Similarity	NPC72817
0.7841	Intermediate Similarity	NPC124172
0.7841	Intermediate Similarity	NPC166279
0.7835	Intermediate Similarity	NPC154452
0.7835	Intermediate Similarity	NPC471889
0.7835	Intermediate Similarity	NPC272015
0.7831	Intermediate Similarity	NPC471723
0.7831	Intermediate Similarity	NPC257347
0.7831	Intermediate Similarity	NPC141071
0.7826	Intermediate Similarity	NPC469738
0.7822	Intermediate Similarity	NPC475243
0.7822	Intermediate Similarity	NPC129340
0.7822	Intermediate Similarity	NPC90630
0.7816	Intermediate Similarity	NPC201852
0.7816	Intermediate Similarity	NPC87489
0.7816	Intermediate Similarity	NPC5985
0.7816	Intermediate Similarity	NPC470049
0.7816	Intermediate Similarity	NPC202389
0.7812	Intermediate Similarity	NPC469942
0.78	Intermediate Similarity	NPC195708
0.7791	Intermediate Similarity	NPC236112
0.7791	Intermediate Similarity	NPC26117
0.7789	Intermediate Similarity	NPC76486
0.7778	Intermediate Similarity	NPC127801
0.7778	Intermediate Similarity	NPC472900
0.7778	Intermediate Similarity	NPC194842
0.7778	Intermediate Similarity	NPC152584
0.7778	Intermediate Similarity	NPC26798
0.7778	Intermediate Similarity	NPC69737
0.7778	Intermediate Similarity	NPC269627
0.7778	Intermediate Similarity	NPC208594
0.7778	Intermediate Similarity	NPC472898
0.7778	Intermediate Similarity	NPC473199
0.7778	Intermediate Similarity	NPC473923
0.7778	Intermediate Similarity	NPC160816
0.7778	Intermediate Similarity	NPC473476
0.7778	Intermediate Similarity	NPC309448
0.7778	Intermediate Similarity	NPC472899
0.7778	Intermediate Similarity	NPC208477
0.7778	Intermediate Similarity	NPC271967
0.7765	Intermediate Similarity	NPC244385
0.7765	Intermediate Similarity	NPC6978
0.7765	Intermediate Similarity	NPC138621
0.7765	Intermediate Similarity	NPC318136
0.7765	Intermediate Similarity	NPC285761
0.7765	Intermediate Similarity	NPC167037
0.7755	Intermediate Similarity	NPC471887
0.7755	Intermediate Similarity	NPC471450
0.7755	Intermediate Similarity	NPC471888
0.7755	Intermediate Similarity	NPC471886
0.7755	Intermediate Similarity	NPC471885
0.7755	Intermediate Similarity	NPC475701
0.7745	Intermediate Similarity	NPC477073
0.7742	Intermediate Similarity	NPC137461
0.7738	Intermediate Similarity	NPC300324
0.7738	Intermediate Similarity	NPC321381
0.7738	Intermediate Similarity	NPC321016
0.7738	Intermediate Similarity	NPC237460
0.7738	Intermediate Similarity	NPC134330
0.7738	Intermediate Similarity	NPC129165
0.7738	Intermediate Similarity	NPC107059
0.7738	Intermediate Similarity	NPC240604
0.7732	Intermediate Similarity	NPC21064
0.7732	Intermediate Similarity	NPC121072
0.7732	Intermediate Similarity	NPC476896
0.7732	Intermediate Similarity	NPC285231
0.7732	Intermediate Similarity	NPC176406
0.7732	Intermediate Similarity	NPC21568
0.7727	Intermediate Similarity	NPC113978
0.7727	Intermediate Similarity	NPC110778
0.7727	Intermediate Similarity	NPC477818
0.7723	Intermediate Similarity	NPC14630
0.7723	Intermediate Similarity	NPC250089
0.7723	Intermediate Similarity	NPC302057
0.7723	Intermediate Similarity	NPC476835
0.7723	Intermediate Similarity	NPC265655
0.7723	Intermediate Similarity	NPC157530
0.7723	Intermediate Similarity	NPC475364
0.7717	Intermediate Similarity	NPC14380
0.7717	Intermediate Similarity	NPC473269
0.7717	Intermediate Similarity	NPC471433
0.7717	Intermediate Similarity	NPC471432
0.7711	Intermediate Similarity	NPC472503
0.7711	Intermediate Similarity	NPC308440
0.7701	Intermediate Similarity	NPC209620
0.7701	Intermediate Similarity	NPC474531
0.7701	Intermediate Similarity	NPC70927
0.7701	Intermediate Similarity	NPC23852
0.77	Intermediate Similarity	NPC33053
0.77	Intermediate Similarity	NPC14946
0.77	Intermediate Similarity	NPC234160

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 NPC16350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2249
0.2-0.3	4359
0.3-0.4	1641
0.4-0.5	348
0.5-0.6	154
0.6-0.7	203
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7619	Intermediate Similarity	NPD6942	Approved
0.7619	Intermediate Similarity	NPD7339	Approved
0.7586	Intermediate Similarity	NPD7525	Registered
0.7586	Intermediate Similarity	NPD4748	Discontinued
0.7471	Intermediate Similarity	NPD7645	Phase 2
0.7386	Intermediate Similarity	NPD6928	Phase 2
0.7326	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6412	Phase 2
0.7065	Intermediate Similarity	NPD4786	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7021	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.6989	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6695	Phase 3
0.6937	Remote Similarity	NPD7516	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.6931	Remote Similarity	NPD7640	Approved
0.6915	Remote Similarity	NPD3618	Phase 1
0.6907	Remote Similarity	NPD6079	Approved
0.6897	Remote Similarity	NPD6924	Approved
0.6897	Remote Similarity	NPD6926	Approved
0.6889	Remote Similarity	NPD6929	Approved
0.6882	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8377	Approved
0.6875	Remote Similarity	NPD8294	Approved
0.686	Remote Similarity	NPD4243	Approved
0.6848	Remote Similarity	NPD3667	Approved
0.6837	Remote Similarity	NPD8171	Discontinued
0.6837	Remote Similarity	NPD6399	Phase 3
0.6814	Remote Similarity	NPD8380	Approved
0.6814	Remote Similarity	NPD8379	Approved
0.6814	Remote Similarity	NPD8296	Approved
0.6814	Remote Similarity	NPD8335	Approved
0.6814	Remote Similarity	NPD8378	Approved
0.6814	Remote Similarity	NPD8033	Approved
0.6814	Remote Similarity	NPD7503	Approved
0.6813	Remote Similarity	NPD6930	Phase 2
0.6813	Remote Similarity	NPD6931	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6742	Remote Similarity	NPD6933	Approved
0.6735	Remote Similarity	NPD8034	Phase 2
0.6735	Remote Similarity	NPD8035	Phase 2
0.6705	Remote Similarity	NPD4785	Approved
0.6705	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6628	Remote Similarity	NPD6923	Approved
0.6628	Remote Similarity	NPD6922	Approved
0.6628	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6370	Approved
0.6607	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD7748	Approved
0.6593	Remote Similarity	NPD6118	Approved
0.6593	Remote Similarity	NPD6114	Approved
0.6593	Remote Similarity	NPD6697	Approved
0.6593	Remote Similarity	NPD6115	Approved
0.6593	Remote Similarity	NPD7145	Approved
0.6581	Remote Similarity	NPD7507	Approved
0.6566	Remote Similarity	NPD7515	Phase 2
0.6562	Remote Similarity	NPD5279	Phase 3
0.6552	Remote Similarity	NPD7143	Approved
0.6552	Remote Similarity	NPD7144	Approved
0.6545	Remote Similarity	NPD6882	Approved
0.6526	Remote Similarity	NPD3133	Approved
0.6526	Remote Similarity	NPD3666	Approved
0.6526	Remote Similarity	NPD3665	Phase 1
0.6522	Remote Similarity	NPD6683	Phase 2
0.6486	Remote Similarity	NPD8133	Approved
0.6481	Remote Similarity	NPD6899	Approved
0.6481	Remote Similarity	NPD6881	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD5222	Approved
0.6471	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5221	Approved
0.6458	Remote Similarity	NPD6893	Approved
0.6452	Remote Similarity	NPD7514	Phase 3
0.6452	Remote Similarity	NPD7509	Discontinued
0.6444	Remote Similarity	NPD5275	Approved
0.6444	Remote Similarity	NPD4190	Phase 3
0.6444	Remote Similarity	NPD8264	Approved
0.6435	Remote Similarity	NPD6059	Approved
0.6435	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6372	Approved
0.6422	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD7319	Approved
0.641	Remote Similarity	NPD6067	Discontinued
0.6408	Remote Similarity	NPD7902	Approved
0.6408	Remote Similarity	NPD6084	Phase 2
0.6408	Remote Similarity	NPD5173	Approved
0.6408	Remote Similarity	NPD4755	Approved
0.6408	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD7087	Discontinued
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6392	Remote Similarity	NPD6409	Approved
0.6389	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD5697	Approved
0.6387	Remote Similarity	NPD8293	Discontinued
0.6383	Remote Similarity	NPD4139	Approved
0.6383	Remote Similarity	NPD4692	Approved
0.6383	Remote Similarity	NPD6902	Approved
0.6381	Remote Similarity	NPD4159	Approved
0.6374	Remote Similarity	NPD6117	Approved
0.6373	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD4787	Phase 1
0.6344	Remote Similarity	NPD4195	Approved
0.6333	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1811	Approved
0.6333	Remote Similarity	NPD1810	Approved
0.633	Remote Similarity	NPD6686	Approved
0.633	Remote Similarity	NPD6011	Approved
0.6316	Remote Similarity	NPD6009	Approved
0.6306	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD8130	Phase 1
0.6306	Remote Similarity	NPD6847	Approved
0.6306	Remote Similarity	NPD6649	Approved
0.6306	Remote Similarity	NPD6869	Approved
0.6306	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6617	Approved
0.6304	Remote Similarity	NPD6116	Phase 1
0.6292	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5286	Approved
0.6286	Remote Similarity	NPD4700	Approved
0.6286	Remote Similarity	NPD4696	Approved
0.6286	Remote Similarity	NPD5285	Approved
0.6277	Remote Similarity	NPD7332	Phase 2
0.6273	Remote Similarity	NPD6012	Approved
0.6273	Remote Similarity	NPD6014	Approved
0.6273	Remote Similarity	NPD6013	Approved
0.6271	Remote Similarity	NPD8328	Phase 3
0.6264	Remote Similarity	NPD3703	Phase 2
0.6263	Remote Similarity	NPD6672	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD6015	Approved
0.6239	Remote Similarity	NPD6016	Approved
0.6238	Remote Similarity	NPD7637	Suspended
0.6238	Remote Similarity	NPD6411	Approved
0.6237	Remote Similarity	NPD3617	Approved
0.6226	Remote Similarity	NPD5223	Approved
0.6218	Remote Similarity	NPD7492	Approved
0.6214	Remote Similarity	NPD7991	Discontinued
0.6211	Remote Similarity	NPD6898	Phase 1
0.6204	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4753	Phase 2
0.6195	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD5290	Discontinued
0.6186	Remote Similarity	NPD3668	Phase 3
0.6186	Remote Similarity	NPD5988	Approved
0.6174	Remote Similarity	NPD7115	Discovery
0.6168	Remote Similarity	NPD5211	Phase 2
0.6168	Remote Similarity	NPD5226	Approved
0.6168	Remote Similarity	NPD4633	Approved
0.6168	Remote Similarity	NPD5225	Approved
0.6168	Remote Similarity	NPD5224	Approved
0.6167	Remote Similarity	NPD6616	Approved
0.6147	Remote Similarity	NPD6008	Approved
0.6146	Remote Similarity	NPD4223	Phase 3
0.6146	Remote Similarity	NPD4221	Approved
0.6129	Remote Similarity	NPD8449	Approved
0.6126	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5329	Approved
0.6117	Remote Similarity	NPD7900	Approved
0.6117	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7078	Approved
0.6111	Remote Similarity	NPD5174	Approved
0.6111	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD6868	Approved
0.6082	Remote Similarity	NPD4788	Approved
0.608	Remote Similarity	NPD8450	Suspended
0.6071	Remote Similarity	NPD4634	Approved
0.6067	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3700	Clinical (unspecified phase)

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