NPASS Compound

Structure

NPC269684 OpenBabel07101718242D 33 37 0 0 1 0 0 0 0 0999 V2000 -2.7817 0.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3022 2.0533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5463 0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5726 0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 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 2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9026 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 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 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 23 1 0 0 0 0 18 27 1 6 0 0 0 19 24 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 1 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 25 1 6 0 0 0 22 33 1 0 0 0 0 23 29 1 1 0 0 0 23 33 1 0 0 0 0 25 31 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 1 0 0 0 28 7 1 1 0 0 0 29 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.36
Volume:	499.882
LogP:	4.606
LogD:	4.122
LogS:	-4.736
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	4.991
Fsp3:	0.966
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:	-4.924
MDCK Permeability:	1.4182209270074964e-05
Pgp-inhibitor:	0.812
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.631
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.792
Plasma Protein Binding (PPB):	88.41311645507812%
Volume Distribution (VD):	1.034
Pgp-substrate:	5.0296454429626465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.386
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	6.039
Half-life (T1/2):	0.269

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.537
Carcinogencity:	0.177
Eye Corrosion:	0.159
Eye Irritation:	0.105
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC269684

Natural Product ID:	NPC269684
*Common Name:**	NNNRTJSRGAXLIH-MTSNUVQISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NNNRTJSRGAXLIH-MTSNUVQISA-N
Standard InCHI:	InChI=1S/C29H48O4/c1-24(2)19-10-14-28(7)20(26(19,5)13-11-21(24)30)9-8-18-23-29(32,17-16-27(18,28)6)15-12-22(33-23)25(3,4)31/h18-20,22-23,31-32H,8-17H2,1-7H3/t18-,19-,20-,22+,23-,26+,27-,28-,29-/m1/s1
SMILES:	CC1(C)[C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@H]5[C@@](CC[C@@H](C(C)(C)O)O5)(CC[C@@]34C)O)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651032
PubChem CID:	50901039
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22817615]
NPO8087	Aglaia foveolata	Species	Meliaceae	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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[506969]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[506969]

☑ 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 NPC269684 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	490
0.1-0.2	3526
0.2-0.3	9039
0.3-0.4	15246
0.4-0.5	5937
0.5-0.6	4473
0.6-0.7	3064
0.7-0.8	862
0.8-0.85	40
0.85-0.9	19
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8506	High Similarity	NPC18536
0.8506	High Similarity	NPC50443
0.8506	High Similarity	NPC472146
0.8506	High Similarity	NPC185529
0.8462	Intermediate Similarity	NPC81759
0.8276	Intermediate Similarity	NPC476379
0.8256	Intermediate Similarity	NPC80700
0.8235	Intermediate Similarity	NPC34984
0.8235	Intermediate Similarity	NPC25037
0.8228	Intermediate Similarity	NPC68426
0.8228	Intermediate Similarity	NPC282905
0.8228	Intermediate Similarity	NPC477229
0.8171	Intermediate Similarity	NPC243594
0.8171	Intermediate Similarity	NPC31031
0.8161	Intermediate Similarity	NPC202937
0.8161	Intermediate Similarity	NPC470920
0.8148	Intermediate Similarity	NPC108840
0.814	Intermediate Similarity	NPC131350
0.8125	Intermediate Similarity	NPC159325
0.8125	Intermediate Similarity	NPC168511
0.8118	Intermediate Similarity	NPC472744
0.8101	Intermediate Similarity	NPC247195
0.8095	Intermediate Similarity	NPC476071
0.8095	Intermediate Similarity	NPC50658
0.8085	Intermediate Similarity	NPC477172
0.8072	Intermediate Similarity	NPC245029
0.8072	Intermediate Similarity	NPC31302
0.8043	Intermediate Similarity	NPC163685
0.8043	Intermediate Similarity	NPC235109
0.8025	Intermediate Similarity	NPC267753
0.8023	Intermediate Similarity	NPC473299
0.8023	Intermediate Similarity	NPC237938
0.8023	Intermediate Similarity	NPC105895
0.8023	Intermediate Similarity	NPC219535
0.8	Intermediate Similarity	NPC121121
0.8	Intermediate Similarity	NPC80640
0.7979	Intermediate Similarity	NPC80417
0.7955	Intermediate Similarity	NPC263802
0.7952	Intermediate Similarity	NPC478084
0.7952	Intermediate Similarity	NPC472608
0.7935	Intermediate Similarity	NPC82633
0.7912	Intermediate Similarity	NPC472147
0.7912	Intermediate Similarity	NPC472148
0.7907	Intermediate Similarity	NPC217559
0.7907	Intermediate Similarity	NPC292458
0.7907	Intermediate Similarity	NPC268578
0.7901	Intermediate Similarity	NPC130011
0.7882	Intermediate Similarity	NPC48756
0.7882	Intermediate Similarity	NPC280781
0.7882	Intermediate Similarity	NPC271572
0.7882	Intermediate Similarity	NPC474870
0.7872	Intermediate Similarity	NPC472144
0.7848	Intermediate Similarity	NPC470833
0.7841	Intermediate Similarity	NPC472745
0.7841	Intermediate Similarity	NPC476727
0.7841	Intermediate Similarity	NPC248216
0.7841	Intermediate Similarity	NPC476726
0.7841	Intermediate Similarity	NPC83242
0.7835	Intermediate Similarity	NPC267637
0.7831	Intermediate Similarity	NPC112463
0.7831	Intermediate Similarity	NPC23884
0.7805	Intermediate Similarity	NPC174964
0.7805	Intermediate Similarity	NPC195155
0.7805	Intermediate Similarity	NPC97534
0.7791	Intermediate Similarity	NPC61107
0.7791	Intermediate Similarity	NPC289486
0.7791	Intermediate Similarity	NPC268040
0.7778	Intermediate Similarity	NPC471459
0.7778	Intermediate Similarity	NPC67653
0.7766	Intermediate Similarity	NPC472145
0.7765	Intermediate Similarity	NPC261616
0.7765	Intermediate Similarity	NPC470609
0.7755	Intermediate Similarity	NPC273189
0.7755	Intermediate Similarity	NPC184805
0.7738	Intermediate Similarity	NPC26029
0.7727	Intermediate Similarity	NPC62572
0.7722	Intermediate Similarity	NPC475977
0.7722	Intermediate Similarity	NPC103647
0.7722	Intermediate Similarity	NPC2568
0.7722	Intermediate Similarity	NPC260319
0.7722	Intermediate Similarity	NPC475893
0.7722	Intermediate Similarity	NPC180777
0.7711	Intermediate Similarity	NPC5767
0.7711	Intermediate Similarity	NPC475742
0.7701	Intermediate Similarity	NPC227170
0.7692	Intermediate Similarity	NPC470114
0.7677	Intermediate Similarity	NPC471430
0.7674	Intermediate Similarity	NPC329490
0.7674	Intermediate Similarity	NPC469745
0.7674	Intermediate Similarity	NPC328639
0.7667	Intermediate Similarity	NPC476435
0.7667	Intermediate Similarity	NPC473319
0.7667	Intermediate Similarity	NPC131104
0.7667	Intermediate Similarity	NPC236459
0.7667	Intermediate Similarity	NPC3032
0.7647	Intermediate Similarity	NPC201276
0.7647	Intermediate Similarity	NPC73013
0.7647	Intermediate Similarity	NPC80891
0.764	Intermediate Similarity	NPC472272
0.764	Intermediate Similarity	NPC474448
0.764	Intermediate Similarity	NPC474215
0.764	Intermediate Similarity	NPC475729
0.7634	Intermediate Similarity	NPC309127
0.7634	Intermediate Similarity	NPC247877
0.7619	Intermediate Similarity	NPC64081
0.7619	Intermediate Similarity	NPC474574
0.7619	Intermediate Similarity	NPC475031
0.7619	Intermediate Similarity	NPC221420
0.7614	Intermediate Similarity	NPC50438
0.7614	Intermediate Similarity	NPC473336
0.7614	Intermediate Similarity	NPC471044
0.7614	Intermediate Similarity	NPC474996
0.7604	Intermediate Similarity	NPC20028
0.7604	Intermediate Similarity	NPC41843
0.7595	Intermediate Similarity	NPC204233
0.759	Intermediate Similarity	NPC159789
0.7586	Intermediate Similarity	NPC154043
0.7586	Intermediate Similarity	NPC60018
0.7586	Intermediate Similarity	NPC477286
0.7586	Intermediate Similarity	NPC286719
0.7586	Intermediate Similarity	NPC202688
0.7579	Intermediate Similarity	NPC472273
0.7579	Intermediate Similarity	NPC272451
0.7579	Intermediate Similarity	NPC471241
0.7579	Intermediate Similarity	NPC470425
0.7576	Intermediate Similarity	NPC119628
0.7576	Intermediate Similarity	NPC477877
0.7576	Intermediate Similarity	NPC158367
0.7576	Intermediate Similarity	NPC158051
0.7564	Intermediate Similarity	NPC260116
0.7561	Intermediate Similarity	NPC232112
0.7558	Intermediate Similarity	NPC472853
0.7553	Intermediate Similarity	NPC17336
0.7551	Intermediate Similarity	NPC225238
0.7551	Intermediate Similarity	NPC107385
0.7551	Intermediate Similarity	NPC34562
0.7529	Intermediate Similarity	NPC34046
0.7529	Intermediate Similarity	NPC324700
0.7529	Intermediate Similarity	NPC171426
0.7529	Intermediate Similarity	NPC224802
0.7529	Intermediate Similarity	NPC80089
0.7527	Intermediate Similarity	NPC291373
0.7527	Intermediate Similarity	NPC474379
0.7526	Intermediate Similarity	NPC54909
0.7526	Intermediate Similarity	NPC233012
0.7526	Intermediate Similarity	NPC178853
0.7525	Intermediate Similarity	NPC87393
0.75	Intermediate Similarity	NPC88337
0.75	Intermediate Similarity	NPC475056
0.75	Intermediate Similarity	NPC40716
0.75	Intermediate Similarity	NPC475234
0.75	Intermediate Similarity	NPC138219
0.75	Intermediate Similarity	NPC477285
0.75	Intermediate Similarity	NPC475211
0.75	Intermediate Similarity	NPC77756
0.75	Intermediate Similarity	NPC475630
0.75	Intermediate Similarity	NPC111582
0.75	Intermediate Similarity	NPC126753
0.7475	Intermediate Similarity	NPC469827
0.7474	Intermediate Similarity	NPC477264
0.7474	Intermediate Similarity	NPC25848
0.7474	Intermediate Similarity	NPC476728
0.7474	Intermediate Similarity	NPC91439
0.7474	Intermediate Similarity	NPC19376
0.7474	Intermediate Similarity	NPC307282
0.7474	Intermediate Similarity	NPC230151
0.7474	Intermediate Similarity	NPC116683
0.7474	Intermediate Similarity	NPC305464
0.7474	Intermediate Similarity	NPC475785
0.7473	Intermediate Similarity	NPC471221
0.7471	Intermediate Similarity	NPC12933
0.7471	Intermediate Similarity	NPC470154
0.7471	Intermediate Similarity	NPC77311
0.7471	Intermediate Similarity	NPC73515
0.7471	Intermediate Similarity	NPC190940
0.747	Intermediate Similarity	NPC74639
0.7451	Intermediate Similarity	NPC470622
0.7451	Intermediate Similarity	NPC66513
0.7449	Intermediate Similarity	NPC471254
0.7449	Intermediate Similarity	NPC80191
0.7449	Intermediate Similarity	NPC470172
0.7449	Intermediate Similarity	NPC310031
0.7447	Intermediate Similarity	NPC296164
0.7447	Intermediate Similarity	NPC277399
0.7444	Intermediate Similarity	NPC120395
0.7442	Intermediate Similarity	NPC477282
0.7442	Intermediate Similarity	NPC81074
0.7442	Intermediate Similarity	NPC220379
0.7439	Intermediate Similarity	NPC131506
0.7439	Intermediate Similarity	NPC89310
0.7439	Intermediate Similarity	NPC156277
0.7439	Intermediate Similarity	NPC290058
0.7439	Intermediate Similarity	NPC157777
0.7439	Intermediate Similarity	NPC127094
0.7439	Intermediate Similarity	NPC58057
0.7439	Intermediate Similarity	NPC157422
0.7439	Intermediate Similarity	NPC151018
0.7439	Intermediate Similarity	NPC100586
0.7439	Intermediate Similarity	NPC109457
0.7439	Intermediate Similarity	NPC320549

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 NPC269684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	554
0.1-0.2	3719
0.2-0.3	3232
0.3-0.4	1066
0.4-0.5	289
0.5-0.6	226
0.6-0.7	50
0.7-0.8	14
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
0.759	Intermediate Similarity	NPD3703	Phase 2
0.7529	Intermediate Similarity	NPD6697	Approved
0.7529	Intermediate Similarity	NPD6115	Approved
0.7529	Intermediate Similarity	NPD6118	Approved
0.7529	Intermediate Similarity	NPD6114	Approved
0.7439	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6116	Phase 1
0.7407	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6117	Approved
0.7284	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5360	Phase 3
0.7184	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4245	Approved
0.7108	Intermediate Similarity	NPD4244	Approved
0.7087	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7748	Approved
0.7059	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7041	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD371	Approved
0.6988	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3698	Phase 2
0.6905	Remote Similarity	NPD4789	Approved
0.6875	Remote Similarity	NPD7515	Phase 2
0.6824	Remote Similarity	NPD4758	Discontinued
0.6824	Remote Similarity	NPD5777	Approved
0.6782	Remote Similarity	NPD3702	Approved
0.6774	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8133	Approved
0.6742	Remote Similarity	NPD5364	Discontinued
0.6742	Remote Similarity	NPD3671	Phase 1
0.6735	Remote Similarity	NPD7900	Approved
0.6735	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8171	Discontinued
0.6628	Remote Similarity	NPD6081	Approved
0.6627	Remote Similarity	NPD4224	Phase 2
0.6593	Remote Similarity	NPD6928	Phase 2
0.6559	Remote Similarity	NPD3669	Approved
0.6559	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1780	Approved
0.6522	Remote Similarity	NPD1779	Approved
0.6522	Remote Similarity	NPD8328	Phase 3
0.6509	Remote Similarity	NPD6412	Phase 2
0.6348	Remote Similarity	NPD6921	Approved
0.6339	Remote Similarity	NPD6940	Discontinued
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7645	Phase 2
0.63	Remote Similarity	NPD6399	Phase 3
0.6292	Remote Similarity	NPD1810	Approved
0.6292	Remote Similarity	NPD1811	Approved
0.6262	Remote Similarity	NPD6920	Discontinued
0.6211	Remote Similarity	NPD4788	Approved
0.619	Remote Similarity	NPD1700	Approved
0.6186	Remote Similarity	NPD3618	Phase 1
0.6162	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD4632	Approved
0.6154	Remote Similarity	NPD7638	Approved
0.6146	Remote Similarity	NPD4786	Approved
0.6139	Remote Similarity	NPD4202	Approved
0.6136	Remote Similarity	NPD2686	Approved
0.6136	Remote Similarity	NPD2687	Approved
0.6136	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2254	Approved
0.6136	Remote Similarity	NPD4787	Phase 1
0.6134	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6105	Remote Similarity	NPD3667	Approved
0.6095	Remote Similarity	NPD8418	Phase 2
0.6095	Remote Similarity	NPD7639	Approved
0.6095	Remote Similarity	NPD7640	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6064	Remote Similarity	NPD7525	Registered
0.6058	Remote Similarity	NPD4755	Approved
0.6055	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6079	Approved
0.6036	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD6899	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5983	Remote Similarity	NPD6059	Approved
0.5983	Remote Similarity	NPD6054	Approved
0.5983	Remote Similarity	NPD6319	Approved
0.5981	Remote Similarity	NPD7632	Discontinued
0.596	Remote Similarity	NPD3573	Approved
0.5946	Remote Similarity	NPD6373	Approved
0.5946	Remote Similarity	NPD6372	Approved
0.5943	Remote Similarity	NPD4700	Approved
0.5943	Remote Similarity	NPD5285	Approved
0.5943	Remote Similarity	NPD5286	Approved
0.5943	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD5697	Approved
0.5909	Remote Similarity	NPD5701	Approved
0.5902	Remote Similarity	NPD7736	Approved
0.59	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7516	Approved
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5888	Remote Similarity	NPD5223	Approved
0.5882	Remote Similarity	NPD6370	Approved
0.5862	Remote Similarity	NPD6009	Approved
0.5859	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6415	Discontinued
0.5856	Remote Similarity	NPD6011	Approved
0.5851	Remote Similarity	NPD4238	Approved
0.5851	Remote Similarity	NPD4802	Phase 2
0.5847	Remote Similarity	NPD8377	Approved
0.5847	Remote Similarity	NPD8294	Approved
0.5842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6649	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6650	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5841	Remote Similarity	NPD6617	Approved
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD7604	Phase 2
0.5818	Remote Similarity	NPD6008	Approved
0.5816	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD3133	Approved
0.5816	Remote Similarity	NPD3665	Phase 1
0.5816	Remote Similarity	NPD3668	Phase 3
0.5814	Remote Similarity	NPD7909	Approved
0.5812	Remote Similarity	NPD7328	Approved
0.5812	Remote Similarity	NPD7327	Approved
0.581	Remote Similarity	NPD4697	Phase 3
0.581	Remote Similarity	NPD5221	Approved
0.581	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5222	Approved
0.5804	Remote Similarity	NPD6013	Approved
0.5804	Remote Similarity	NPD6012	Approved
0.5804	Remote Similarity	NPD6014	Approved
0.5798	Remote Similarity	NPD6015	Approved
0.5798	Remote Similarity	NPD5983	Phase 2
0.5798	Remote Similarity	NPD6016	Approved
0.5798	Remote Similarity	NPD8335	Approved
0.5798	Remote Similarity	NPD8033	Approved
0.5798	Remote Similarity	NPD8380	Approved
0.5798	Remote Similarity	NPD8296	Approved
0.5798	Remote Similarity	NPD8378	Approved
0.5798	Remote Similarity	NPD8379	Approved
0.5789	Remote Similarity	NPD6882	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.578	Remote Similarity	NPD5175	Approved
0.578	Remote Similarity	NPD5174	Approved
0.578	Remote Similarity	NPD4754	Approved
0.5755	Remote Similarity	NPD6084	Phase 2
0.5755	Remote Similarity	NPD5173	Approved
0.5755	Remote Similarity	NPD6083	Phase 2
0.575	Remote Similarity	NPD5988	Approved
0.5738	Remote Similarity	NPD6616	Approved
0.5738	Remote Similarity	NPD6336	Discontinued
0.5727	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD7991	Discontinued
0.5702	Remote Similarity	NPD6067	Discontinued
0.57	Remote Similarity	NPD6409	Approved
0.57	Remote Similarity	NPD5330	Approved
0.57	Remote Similarity	NPD7334	Approved
0.57	Remote Similarity	NPD7521	Approved
0.57	Remote Similarity	NPD6684	Approved
0.57	Remote Similarity	NPD7146	Approved
0.5691	Remote Similarity	NPD7078	Approved
0.5691	Remote Similarity	NPD8293	Discontinued
0.5686	Remote Similarity	NPD4753	Phase 2
0.5684	Remote Similarity	NPD3617	Approved
0.5679	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4767	Approved
0.5676	Remote Similarity	NPD4768	Approved
0.5645	Remote Similarity	NPD6033	Approved
0.5644	Remote Similarity	NPD7524	Approved
0.5612	Remote Similarity	NPD4223	Phase 3
0.5612	Remote Similarity	NPD4221	Approved
0.56	Remote Similarity	NPD5329	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