NPASS Compound

Structure

NPC474448 OpenBabel07101718222D 34 39 0 0 1 0 0 0 0 0999 V2000 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6321 0.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0027 1.0182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8517 2.3785 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8721 -0.1017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0950 0.5276 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 1.7321 -0.0000 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 1.0739 2.4781 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 2.0685 2.5827 0.0000 C 0 0 3 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 0.0000 1.0000 0.0000 C 0 0 1 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 4.7108 0.4430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 1 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 5.6444 0.0846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4533 1.4612 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 2.5685 3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8008 -0.9031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4520 1.4089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 6 0 0 0 20 27 1 1 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 21 32 2 0 0 0 0 22 25 1 6 0 0 0 22 34 1 0 0 0 0 23 26 1 6 0 0 0 23 28 1 0 0 0 0 25 33 1 0 0 0 0 26 27 1 6 0 0 0 27 6 1 1 0 0 0 28 7 1 1 0 0 0 28 34 1 0 0 0 0 29 30 1 1 0 0 0 30 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	508.622
LogP:	4.418
LogD:	3.721
LogS:	-4.411
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	5.785
Fsp3:	0.967
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:	-5.252
MDCK Permeability:	1.2930893717566505e-05
Pgp-inhibitor:	0.513
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.862
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	90.50162506103516%
Volume Distribution (VD):	1.104
Pgp-substrate:	5.625976085662842%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	6.201
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.412
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.64
Carcinogencity:	0.425
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC474448

Natural Product ID:	NPC474448
*Common Name:**	Argentatine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RBRKRLQNZMJOLD-XZRBSSNWSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-24(2)19-8-9-20-27(6)16-18(31)23(28(7)12-11-22(34-28)25(3,4)33)26(27,5)14-15-30(20)17-29(19,30)13-10-21(24)32/h18-20,22-23,31,33H,8-17H2,1-7H3/t18?,19-,20-,22-,23-,26+,27-,28+,29+,30-/m0/s1
SMILES:	OC1C[C@@]2([C@]([C@H]1[C@@]1(C)CC[C@H](O1)C(O)(C)C)(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468867
PubChem CID:	44566816
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO33324	borrichia frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988597]

☑ 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	>	128.0	ug.mL-1	PMID[519185]

☑ 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 NPC474448 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	388
0.1-0.2	3435
0.2-0.3	11821
0.3-0.4	11882
0.4-0.5	5869
0.5-0.6	5867
0.6-0.7	2813
0.7-0.8	561
0.8-0.85	40
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC217559
0.9146	High Similarity	NPC292458
0.9146	High Similarity	NPC268578
0.9125	High Similarity	NPC31302
0.9125	High Similarity	NPC245029
0.9048	High Similarity	NPC472745
0.8916	High Similarity	NPC472744
0.8902	High Similarity	NPC77311
0.8875	High Similarity	NPC264602
0.8824	High Similarity	NPC80700
0.8721	High Similarity	NPC202937
0.869	High Similarity	NPC259173
0.8605	High Similarity	NPC92139
0.8571	High Similarity	NPC475388
0.8571	High Similarity	NPC164289
0.8571	High Similarity	NPC242771
0.8571	High Similarity	NPC311642
0.8571	High Similarity	NPC100366
0.8556	High Similarity	NPC470423
0.8554	High Similarity	NPC472853
0.8554	High Similarity	NPC470609
0.85	High Similarity	NPC472854
0.8452	Intermediate Similarity	NPC469745
0.837	Intermediate Similarity	NPC116683
0.8353	Intermediate Similarity	NPC102156
0.8353	Intermediate Similarity	NPC477935
0.8353	Intermediate Similarity	NPC317066
0.8353	Intermediate Similarity	NPC148740
0.8353	Intermediate Similarity	NPC477936
0.8352	Intermediate Similarity	NPC206878
0.8313	Intermediate Similarity	NPC476732
0.8313	Intermediate Similarity	NPC199965
0.8295	Intermediate Similarity	NPC251808
0.8295	Intermediate Similarity	NPC474174
0.8193	Intermediate Similarity	NPC180199
0.8193	Intermediate Similarity	NPC477919
0.8193	Intermediate Similarity	NPC133596
0.8193	Intermediate Similarity	NPC11907
0.8182	Intermediate Similarity	NPC476727
0.8182	Intermediate Similarity	NPC476726
0.8172	Intermediate Similarity	NPC476728
0.8171	Intermediate Similarity	NPC24014
0.8171	Intermediate Similarity	NPC27349
0.8161	Intermediate Similarity	NPC474996
0.8148	Intermediate Similarity	NPC310766
0.8132	Intermediate Similarity	NPC473066
0.8111	Intermediate Similarity	NPC61688
0.8105	Intermediate Similarity	NPC41843
0.8065	Intermediate Similarity	NPC470031
0.8065	Intermediate Similarity	NPC215570
0.8023	Intermediate Similarity	NPC12933
0.8021	Intermediate Similarity	NPC178853
0.8	Intermediate Similarity	NPC321732
0.8	Intermediate Similarity	NPC81074
0.8	Intermediate Similarity	NPC324607
0.8	Intermediate Similarity	NPC477282
0.7978	Intermediate Similarity	NPC472272
0.7976	Intermediate Similarity	NPC474574
0.7976	Intermediate Similarity	NPC474404
0.7976	Intermediate Similarity	NPC64081
0.7976	Intermediate Similarity	NPC475031
0.7957	Intermediate Similarity	NPC470424
0.7952	Intermediate Similarity	NPC231680
0.7952	Intermediate Similarity	NPC270306
0.7952	Intermediate Similarity	NPC273366
0.7952	Intermediate Similarity	NPC91387
0.7935	Intermediate Similarity	NPC52756
0.7931	Intermediate Similarity	NPC328007
0.7927	Intermediate Similarity	NPC474123
0.7912	Intermediate Similarity	NPC56962
0.7912	Intermediate Similarity	NPC24705
0.7912	Intermediate Similarity	NPC228059
0.7889	Intermediate Similarity	NPC263802
0.7872	Intermediate Similarity	NPC17336
0.7857	Intermediate Similarity	NPC470145
0.7849	Intermediate Similarity	NPC472231
0.7849	Intermediate Similarity	NPC472232
0.7849	Intermediate Similarity	NPC161035
0.7843	Intermediate Similarity	NPC473062
0.7841	Intermediate Similarity	NPC111582
0.7841	Intermediate Similarity	NPC327451
0.7841	Intermediate Similarity	NPC477285
0.7835	Intermediate Similarity	NPC477172
0.7826	Intermediate Similarity	NPC475056
0.7826	Intermediate Similarity	NPC77756
0.7816	Intermediate Similarity	NPC58631
0.7816	Intermediate Similarity	NPC190940
0.7805	Intermediate Similarity	NPC320549
0.7805	Intermediate Similarity	NPC473267
0.7805	Intermediate Similarity	NPC156277
0.7805	Intermediate Similarity	NPC151018
0.7805	Intermediate Similarity	NPC58057
0.7802	Intermediate Similarity	NPC48824
0.7802	Intermediate Similarity	NPC250687
0.7802	Intermediate Similarity	NPC229407
0.7802	Intermediate Similarity	NPC254572
0.7791	Intermediate Similarity	NPC201276
0.7791	Intermediate Similarity	NPC287452
0.7791	Intermediate Similarity	NPC52951
0.7791	Intermediate Similarity	NPC80891
0.7789	Intermediate Similarity	NPC156377
0.7778	Intermediate Similarity	NPC215968
0.7778	Intermediate Similarity	NPC155531
0.7778	Intermediate Similarity	NPC114378
0.7778	Intermediate Similarity	NPC100078
0.7778	Intermediate Similarity	NPC103782
0.7765	Intermediate Similarity	NPC477918
0.7765	Intermediate Similarity	NPC171658
0.7755	Intermediate Similarity	NPC244969
0.7755	Intermediate Similarity	NPC213528
0.7753	Intermediate Similarity	NPC473336
0.7753	Intermediate Similarity	NPC471044
0.7753	Intermediate Similarity	NPC319909
0.7753	Intermediate Similarity	NPC50438
0.7742	Intermediate Similarity	NPC471747
0.7738	Intermediate Similarity	NPC317242
0.7732	Intermediate Similarity	NPC20028
0.7727	Intermediate Similarity	NPC477286
0.7727	Intermediate Similarity	NPC24556
0.7727	Intermediate Similarity	NPC286719
0.7727	Intermediate Similarity	NPC121121
0.7717	Intermediate Similarity	NPC269267
0.7711	Intermediate Similarity	NPC153719
0.7711	Intermediate Similarity	NPC232112
0.77	Intermediate Similarity	NPC166079
0.77	Intermediate Similarity	NPC215408
0.7692	Intermediate Similarity	NPC210658
0.7692	Intermediate Similarity	NPC469322
0.7692	Intermediate Similarity	NPC161928
0.7692	Intermediate Similarity	NPC5943
0.7684	Intermediate Similarity	NPC305808
0.7674	Intermediate Similarity	NPC324700
0.7674	Intermediate Similarity	NPC80089
0.7674	Intermediate Similarity	NPC471045
0.7674	Intermediate Similarity	NPC224802
0.7674	Intermediate Similarity	NPC171426
0.7674	Intermediate Similarity	NPC34046
0.7667	Intermediate Similarity	NPC266651
0.766	Intermediate Similarity	NPC211845
0.766	Intermediate Similarity	NPC476189
0.766	Intermediate Similarity	NPC228700
0.766	Intermediate Similarity	NPC182740
0.766	Intermediate Similarity	NPC256104
0.766	Intermediate Similarity	NPC122083
0.7647	Intermediate Similarity	NPC163597
0.7647	Intermediate Similarity	NPC477932
0.7647	Intermediate Similarity	NPC477933
0.764	Intermediate Similarity	NPC269684
0.7619	Intermediate Similarity	NPC472945
0.7619	Intermediate Similarity	NPC254340
0.7619	Intermediate Similarity	NPC472944
0.7609	Intermediate Similarity	NPC56777
0.7609	Intermediate Similarity	NPC226491
0.7609	Intermediate Similarity	NPC128475
0.7609	Intermediate Similarity	NPC33398
0.7609	Intermediate Similarity	NPC476435
0.7609	Intermediate Similarity	NPC476379
0.7609	Intermediate Similarity	NPC477614
0.7609	Intermediate Similarity	NPC201607
0.759	Intermediate Similarity	NPC469940
0.7586	Intermediate Similarity	NPC269333
0.7582	Intermediate Similarity	NPC131365
0.7582	Intermediate Similarity	NPC477283
0.7582	Intermediate Similarity	NPC302111
0.7579	Intermediate Similarity	NPC30687
0.7579	Intermediate Similarity	NPC217567
0.7579	Intermediate Similarity	NPC175
0.7579	Intermediate Similarity	NPC76136
0.7579	Intermediate Similarity	NPC329713
0.7579	Intermediate Similarity	NPC477495
0.7579	Intermediate Similarity	NPC67831
0.7579	Intermediate Similarity	NPC174051
0.7576	Intermediate Similarity	NPC310031
0.7576	Intermediate Similarity	NPC80191
0.7561	Intermediate Similarity	NPC213178
0.7561	Intermediate Similarity	NPC6120
0.7561	Intermediate Similarity	NPC131892
0.7561	Intermediate Similarity	NPC327728
0.7558	Intermediate Similarity	NPC476233
0.7558	Intermediate Similarity	NPC105208
0.7558	Intermediate Similarity	NPC185915
0.7558	Intermediate Similarity	NPC128951
0.7558	Intermediate Similarity	NPC23884
0.7558	Intermediate Similarity	NPC192046
0.7558	Intermediate Similarity	NPC477227
0.7558	Intermediate Similarity	NPC302578
0.7556	Intermediate Similarity	NPC291310
0.7553	Intermediate Similarity	NPC262870
0.7551	Intermediate Similarity	NPC470030
0.7551	Intermediate Similarity	NPC108371
0.7549	Intermediate Similarity	NPC475319
0.7549	Intermediate Similarity	NPC202898
0.7549	Intermediate Similarity	NPC92890
0.7549	Intermediate Similarity	NPC472079
0.7529	Intermediate Similarity	NPC174964
0.7529	Intermediate Similarity	NPC477934
0.7529	Intermediate Similarity	NPC125767
0.7529	Intermediate Similarity	NPC21220
0.7529	Intermediate Similarity	NPC159789
0.7529	Intermediate Similarity	NPC97534

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 NPC474448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	3619
0.2-0.3	3574
0.3-0.4	885
0.4-0.5	289
0.5-0.6	226
0.6-0.7	112
0.7-0.8	25
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
0.8125	Intermediate Similarity	NPD4244	Approved
0.8125	Intermediate Similarity	NPD4245	Approved
0.8	Intermediate Similarity	NPD3698	Phase 2
0.7805	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4789	Approved
0.7674	Intermediate Similarity	NPD6115	Approved
0.7674	Intermediate Similarity	NPD6118	Approved
0.7674	Intermediate Similarity	NPD6114	Approved
0.7674	Intermediate Similarity	NPD6697	Approved
0.759	Intermediate Similarity	NPD5777	Approved
0.7561	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3703	Phase 2
0.7529	Intermediate Similarity	NPD3702	Approved
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6117	Approved
0.7439	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5360	Phase 3
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.7349	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4788	Approved
0.7176	Intermediate Similarity	NPD6081	Approved
0.7113	Intermediate Similarity	NPD8171	Discontinued
0.7111	Intermediate Similarity	NPD6928	Phase 2
0.6988	Remote Similarity	NPD4224	Phase 2
0.6977	Remote Similarity	NPD4758	Discontinued
0.6952	Remote Similarity	NPD6412	Phase 2
0.6889	Remote Similarity	NPD3671	Phase 1
0.6889	Remote Similarity	NPD5364	Discontinued
0.686	Remote Similarity	NPD4787	Phase 1
0.6832	Remote Similarity	NPD6083	Phase 2
0.6832	Remote Similarity	NPD6084	Phase 2
0.6804	Remote Similarity	NPD4753	Phase 2
0.6796	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4786	Approved
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3133	Approved
0.6632	Remote Similarity	NPD3665	Phase 1
0.6577	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6562	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6370	Approved
0.6542	Remote Similarity	NPD6402	Approved
0.6542	Remote Similarity	NPD5739	Approved
0.6542	Remote Similarity	NPD6675	Approved
0.6542	Remote Similarity	NPD7128	Approved
0.6505	Remote Similarity	NPD4755	Approved
0.65	Remote Similarity	NPD8034	Phase 2
0.65	Remote Similarity	NPD8035	Phase 2
0.6486	Remote Similarity	NPD8297	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD5695	Phase 3
0.6471	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD6016	Approved
0.6466	Remote Similarity	NPD6015	Approved
0.6455	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD5696	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6436	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD4632	Approved
0.6422	Remote Similarity	NPD6881	Approved
0.6422	Remote Similarity	NPD6899	Approved
0.6421	Remote Similarity	NPD3667	Approved
0.6421	Remote Similarity	NPD4223	Phase 3
0.6421	Remote Similarity	NPD4221	Approved
0.6417	Remote Similarity	NPD7736	Approved
0.641	Remote Similarity	NPD5988	Approved
0.6392	Remote Similarity	NPD5329	Approved
0.6389	Remote Similarity	NPD6008	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6381	Remote Similarity	NPD5285	Approved
0.6381	Remote Similarity	NPD4700	Approved
0.6381	Remote Similarity	NPD4696	Approved
0.6381	Remote Similarity	NPD5286	Approved
0.6379	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7604	Phase 2
0.6344	Remote Similarity	NPD4802	Phase 2
0.6344	Remote Similarity	NPD4238	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD7078	Approved
0.633	Remote Similarity	NPD5697	Approved
0.633	Remote Similarity	NPD5701	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD4139	Approved
0.6316	Remote Similarity	NPD4692	Approved
0.6316	Remote Similarity	NPD6940	Discontinued
0.6306	Remote Similarity	NPD7102	Approved
0.6306	Remote Similarity	NPD6883	Approved
0.6306	Remote Similarity	NPD7290	Approved
0.63	Remote Similarity	NPD5328	Approved
0.6289	Remote Similarity	NPD4197	Approved
0.6286	Remote Similarity	NPD7638	Approved
0.6273	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3198	Approved
0.6263	Remote Similarity	NPD7524	Approved
0.6262	Remote Similarity	NPD5226	Approved
0.6262	Remote Similarity	NPD5225	Approved
0.6262	Remote Similarity	NPD4633	Approved
0.6262	Remote Similarity	NPD5224	Approved
0.6262	Remote Similarity	NPD5211	Phase 2
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6920	Discontinued
0.623	Remote Similarity	NPD7319	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD8418	Phase 2
0.6226	Remote Similarity	NPD7640	Approved
0.6216	Remote Similarity	NPD6013	Approved
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6014	Approved
0.6216	Remote Similarity	NPD6012	Approved
0.6214	Remote Similarity	NPD6001	Approved
0.6204	Remote Similarity	NPD5175	Approved
0.6204	Remote Similarity	NPD5174	Approved
0.6195	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD5223	Approved
0.6162	Remote Similarity	NPD3618	Phase 1
0.6162	Remote Similarity	NPD4688	Approved
0.6162	Remote Similarity	NPD5205	Approved
0.6162	Remote Similarity	NPD4690	Approved
0.6162	Remote Similarity	NPD6098	Approved
0.6162	Remote Similarity	NPD4693	Phase 3
0.6162	Remote Similarity	NPD4138	Approved
0.6162	Remote Similarity	NPD4689	Approved
0.6154	Remote Similarity	NPD7991	Discontinued
0.6148	Remote Similarity	NPD6033	Approved
0.6147	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5141	Approved
0.6139	Remote Similarity	NPD6904	Approved
0.6139	Remote Similarity	NPD6673	Approved
0.6139	Remote Similarity	NPD6080	Approved
0.6126	Remote Similarity	NPD6011	Approved
0.6121	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD7632	Discontinued
0.6106	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4768	Approved
0.6091	Remote Similarity	NPD4767	Approved
0.6083	Remote Similarity	NPD6067	Discontinued
0.6071	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7328	Approved
0.6068	Remote Similarity	NPD7327	Approved
0.6055	Remote Similarity	NPD4754	Approved
0.605	Remote Similarity	NPD5983	Phase 2
0.6048	Remote Similarity	NPD5956	Approved
0.6042	Remote Similarity	NPD7525	Registered
0.604	Remote Similarity	NPD6672	Approved
0.604	Remote Similarity	NPD5737	Approved
0.602	Remote Similarity	NPD6695	Phase 3
0.6017	Remote Similarity	NPD4522	Approved
0.6017	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4694	Approved
0.6	Remote Similarity	NPD5280	Approved
0.6	Remote Similarity	NPD5690	Phase 2
0.6	Remote Similarity	NPD3617	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.5984	Remote Similarity	NPD6336	Discontinued
0.5982	Remote Similarity	NPD5128	Approved
0.5982	Remote Similarity	NPD4729	Approved
0.5982	Remote Similarity	NPD4730	Approved
0.5982	Remote Similarity	NPD6686	Approved
0.5977	Remote Similarity	NPD371	Approved
0.5966	Remote Similarity	NPD8294	Approved
0.5966	Remote Similarity	NPD8377	Approved
0.5962	Remote Similarity	NPD5133	Approved
0.596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.596	Remote Similarity	NPD3668	Phase 3
0.5943	Remote Similarity	NPD5222	Approved
0.5943	Remote Similarity	NPD4697	Phase 3
0.5943	Remote Similarity	NPD5221	Approved
0.5943	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5207	Approved
0.5917	Remote Similarity	NPD8335	Approved
0.5917	Remote Similarity	NPD8296	Approved
0.5917	Remote Similarity	NPD8378	Approved
0.5917	Remote Similarity	NPD8380	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