NPASS Compound

Structure

NPC116320 OpenBabel07101719252D 43 45 0 0 1 0 0 0 0 0999 V2000 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9049 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0012 -0.7421 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 -3.0972 0.8035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9049 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 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 -3.9049 -4.5981 0.0000 C 0 0 0 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 -3.4049 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9927 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0501 -1.0511 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 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3559 -0.6910 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 -2.4049 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9927 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 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 -4.8422 -2.0292 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9049 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9062 0.2158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3070 -0.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9049 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 18 33 2 0 0 0 0 18 39 1 0 0 0 0 19 34 2 0 0 0 0 19 40 1 0 0 0 0 20 16 1 6 0 0 0 20 26 1 0 0 0 0 20 41 1 0 0 0 0 21 30 1 6 0 0 0 21 39 1 0 0 0 0 22 35 2 0 0 0 0 22 42 1 0 0 0 0 23 36 2 0 0 0 0 23 43 1 0 0 0 0 24 17 1 6 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 42 1 0 0 0 0 28 31 1 0 0 0 0 28 41 1 0 0 0 0 29 32 1 0 0 0 0 29 40 1 0 0 0 0 30 37 1 0 0 0 0 31 43 1 0 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.35
Volume:	622.505
LogP:	4.086
LogD:	2.675
LogS:	-3.791
# Rotatable Bonds:	13
TPSA:	154.89
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	6.355
Fsp3:	0.875
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838
MDCK Permeability:	0.00012103574408683926
Pgp-inhibitor:	0.999
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	81.50147247314453%
Volume Distribution (VD):	1.255
Pgp-substrate:	7.761462688446045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.306
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.563
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	3.7
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.839
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.197
Carcinogencity:	0.038
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC116320

Natural Product ID:	NPC116320
*Common Name:**	Simplexin C
IUPAC Name:	n.a.
Synonyms:	Simplexin C
Standard InCHIKey:	HCQIFRTWVUQXOW-YCZQKTHSSA-N
Standard InCHI:	InChI=1S/C32H52O11/c1-10-12-22(35)42-27-24(17(3)4)25-26(32(9,38)29(27)40-19(6)34)20-16-30(7,37)21(39-18(5)33)14-15-31(8,28(25)41-20)43-23(36)13-11-2/h17,20-21,24-29,37-38H,10-16H2,1-9H3/t20-,21+,24-,25-,26-,27+,28-,29-,30+,31-,32+/m1/s1
SMILES:	CCCC(=O)O[C@]1(C)CC[C@H](OC(=O)C)[C@@](C[C@H]2O[C@@H]1[C@@H]1[C@@H](C(C)C)[C@H](OC(=O)CCC)[C@H]([C@@]([C@H]21)(C)O)OC(=O)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL552730
PubChem CID:	44179258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane diterpenoids

*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
NPO6535	Klyxum simplex	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19391605]
NPO6535	Klyxum simplex	Species	Alcyoniidae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529768]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529768]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529768]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529768]

☑ 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 NPC116320 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	381
0.1-0.2	3256
0.2-0.3	9135
0.3-0.4	14737
0.4-0.5	6779
0.5-0.6	6900
0.6-0.7	1378
0.7-0.8	94
0.8-0.85	20
0.85-0.9	7
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC119922
0.9737	High Similarity	NPC211049
0.9375	High Similarity	NPC228593
0.9375	High Similarity	NPC235196
0.9351	High Similarity	NPC186594
0.9342	High Similarity	NPC191345
0.9342	High Similarity	NPC43463
0.9342	High Similarity	NPC252483
0.9114	High Similarity	NPC216800
0.9079	High Similarity	NPC136424
0.8961	High Similarity	NPC476719
0.8824	High Similarity	NPC41838
0.875	High Similarity	NPC470154
0.8706	High Similarity	NPC470262
0.8675	High Similarity	NPC246347
0.8642	High Similarity	NPC477447
0.8642	High Similarity	NPC470155
0.8642	High Similarity	NPC477446
0.8571	High Similarity	NPC471377
0.8554	High Similarity	NPC476715
0.8554	High Similarity	NPC93616
0.8519	High Similarity	NPC470156
0.8452	Intermediate Similarity	NPC279260
0.8442	Intermediate Similarity	NPC476718
0.8276	Intermediate Similarity	NPC471378
0.8276	Intermediate Similarity	NPC312471
0.8235	Intermediate Similarity	NPC477283
0.8182	Intermediate Similarity	NPC122057
0.8182	Intermediate Similarity	NPC312805
0.8171	Intermediate Similarity	NPC472951
0.8171	Intermediate Similarity	NPC472943
0.8161	Intermediate Similarity	NPC291875
0.809	Intermediate Similarity	NPC475307
0.8068	Intermediate Similarity	NPC470114
0.8046	Intermediate Similarity	NPC92370
0.8046	Intermediate Similarity	NPC470260
0.8046	Intermediate Similarity	NPC476435
0.8046	Intermediate Similarity	NPC75443
0.8023	Intermediate Similarity	NPC215968
0.8023	Intermediate Similarity	NPC155531
0.8023	Intermediate Similarity	NPC476717
0.7978	Intermediate Similarity	NPC91251
0.7975	Intermediate Similarity	NPC123122
0.7931	Intermediate Similarity	NPC44538
0.7931	Intermediate Similarity	NPC213658
0.7931	Intermediate Similarity	NPC110365
0.7931	Intermediate Similarity	NPC62202
0.7931	Intermediate Similarity	NPC45833
0.7882	Intermediate Similarity	NPC239308
0.7882	Intermediate Similarity	NPC470261
0.7882	Intermediate Similarity	NPC476721
0.7841	Intermediate Similarity	NPC201607
0.7841	Intermediate Similarity	NPC476379
0.7841	Intermediate Similarity	NPC56777
0.7816	Intermediate Similarity	NPC475684
0.7791	Intermediate Similarity	NPC18953
0.7766	Intermediate Similarity	NPC272223
0.7765	Intermediate Similarity	NPC477284
0.7765	Intermediate Similarity	NPC154043
0.7765	Intermediate Similarity	NPC60018
0.7765	Intermediate Similarity	NPC202688
0.7765	Intermediate Similarity	NPC286719
0.7765	Intermediate Similarity	NPC477286
0.7753	Intermediate Similarity	NPC161560
0.7701	Intermediate Similarity	NPC196911
0.7701	Intermediate Similarity	NPC477445
0.7701	Intermediate Similarity	NPC266651
0.7701	Intermediate Similarity	NPC471379
0.7674	Intermediate Similarity	NPC111582
0.7674	Intermediate Similarity	NPC477285
0.7654	Intermediate Similarity	NPC470151
0.7647	Intermediate Similarity	NPC118116
0.7647	Intermediate Similarity	NPC190940
0.764	Intermediate Similarity	NPC471221
0.764	Intermediate Similarity	NPC476724
0.764	Intermediate Similarity	NPC470872
0.764	Intermediate Similarity	NPC476723
0.7614	Intermediate Similarity	NPC474008
0.7614	Intermediate Similarity	NPC471410
0.7614	Intermediate Similarity	NPC131365
0.7614	Intermediate Similarity	NPC471411
0.7614	Intermediate Similarity	NPC103782
0.7614	Intermediate Similarity	NPC114378
0.7582	Intermediate Similarity	NPC473066
0.7561	Intermediate Similarity	NPC472950
0.7561	Intermediate Similarity	NPC472952
0.7553	Intermediate Similarity	NPC111348
0.7551	Intermediate Similarity	NPC470263
0.7529	Intermediate Similarity	NPC474714
0.7528	Intermediate Similarity	NPC5943
0.75	Intermediate Similarity	NPC476725
0.7473	Intermediate Similarity	NPC50443
0.7473	Intermediate Similarity	NPC18536
0.7471	Intermediate Similarity	NPC127917
0.7471	Intermediate Similarity	NPC69953
0.7471	Intermediate Similarity	NPC5958
0.7447	Intermediate Similarity	NPC235109
0.7447	Intermediate Similarity	NPC116683
0.7444	Intermediate Similarity	NPC309656
0.7442	Intermediate Similarity	NPC475743
0.7416	Intermediate Similarity	NPC64862
0.7412	Intermediate Similarity	NPC477287
0.7391	Intermediate Similarity	NPC216137
0.7386	Intermediate Similarity	NPC473299
0.7386	Intermediate Similarity	NPC65133
0.7386	Intermediate Similarity	NPC477434
0.7363	Intermediate Similarity	NPC477443
0.7363	Intermediate Similarity	NPC477440
0.7356	Intermediate Similarity	NPC311642
0.7356	Intermediate Similarity	NPC242771
0.7356	Intermediate Similarity	NPC164289
0.7356	Intermediate Similarity	NPC100366
0.7356	Intermediate Similarity	NPC103171
0.734	Intermediate Similarity	NPC82633
0.734	Intermediate Similarity	NPC57964
0.734	Intermediate Similarity	NPC94582
0.7326	Intermediate Similarity	NPC186588
0.7326	Intermediate Similarity	NPC471217
0.7326	Intermediate Similarity	NPC471216
0.732	Intermediate Similarity	NPC98225
0.7312	Intermediate Similarity	NPC256104
0.7312	Intermediate Similarity	NPC211845
0.7312	Intermediate Similarity	NPC122083
0.7312	Intermediate Similarity	NPC182740
0.7303	Intermediate Similarity	NPC478111
0.7303	Intermediate Similarity	NPC235402
0.7292	Intermediate Similarity	NPC472144
0.7283	Intermediate Similarity	NPC472146
0.7283	Intermediate Similarity	NPC477442
0.7283	Intermediate Similarity	NPC477433
0.7283	Intermediate Similarity	NPC477444
0.7283	Intermediate Similarity	NPC185529
0.7273	Intermediate Similarity	NPC241959
0.7273	Intermediate Similarity	NPC15091
0.7273	Intermediate Similarity	NPC29342
0.7273	Intermediate Similarity	NPC2572
0.7263	Intermediate Similarity	NPC163685
0.7263	Intermediate Similarity	NPC203434
0.7263	Intermediate Similarity	NPC238796
0.7263	Intermediate Similarity	NPC475765
0.7263	Intermediate Similarity	NPC475785
0.7263	Intermediate Similarity	NPC237071
0.7241	Intermediate Similarity	NPC71541
0.7241	Intermediate Similarity	NPC73515
0.7241	Intermediate Similarity	NPC77003
0.7234	Intermediate Similarity	NPC191915
0.7234	Intermediate Similarity	NPC151214
0.7229	Intermediate Similarity	NPC166250
0.7229	Intermediate Similarity	NPC55508
0.7229	Intermediate Similarity	NPC472944
0.7229	Intermediate Similarity	NPC472945
0.7222	Intermediate Similarity	NPC268633
0.7222	Intermediate Similarity	NPC321812
0.7222	Intermediate Similarity	NPC322922
0.7216	Intermediate Similarity	NPC51579
0.7216	Intermediate Similarity	NPC477656
0.7216	Intermediate Similarity	NPC188968
0.7209	Intermediate Similarity	NPC476176
0.7209	Intermediate Similarity	NPC477282
0.7209	Intermediate Similarity	NPC81074
0.7204	Intermediate Similarity	NPC165180
0.7204	Intermediate Similarity	NPC219516
0.7188	Intermediate Similarity	NPC472145
0.7176	Intermediate Similarity	NPC307865
0.7176	Intermediate Similarity	NPC212453
0.7172	Intermediate Similarity	NPC61442
0.7159	Intermediate Similarity	NPC2096
0.7159	Intermediate Similarity	NPC121121
0.7159	Intermediate Similarity	NPC208912
0.7159	Intermediate Similarity	NPC102156
0.7159	Intermediate Similarity	NPC148740
0.7143	Intermediate Similarity	NPC239938
0.7143	Intermediate Similarity	NPC186851
0.7143	Intermediate Similarity	NPC475574
0.7143	Intermediate Similarity	NPC36479
0.7126	Intermediate Similarity	NPC16449
0.7125	Intermediate Similarity	NPC476928
0.7113	Intermediate Similarity	NPC253995
0.7113	Intermediate Similarity	NPC209798
0.7113	Intermediate Similarity	NPC292775
0.7113	Intermediate Similarity	NPC471374
0.7113	Intermediate Similarity	NPC471375
0.7093	Intermediate Similarity	NPC272841
0.7083	Intermediate Similarity	NPC296936
0.7083	Intermediate Similarity	NPC129569
0.7083	Intermediate Similarity	NPC156377
0.7083	Intermediate Similarity	NPC292718
0.7083	Intermediate Similarity	NPC111834
0.7083	Intermediate Similarity	NPC306797
0.7083	Intermediate Similarity	NPC252056
0.7083	Intermediate Similarity	NPC169270
0.7079	Intermediate Similarity	NPC474253
0.7079	Intermediate Similarity	NPC474346
0.7079	Intermediate Similarity	NPC475820
0.7079	Intermediate Similarity	NPC269684
0.7079	Intermediate Similarity	NPC474284
0.7079	Intermediate Similarity	NPC213737
0.7079	Intermediate Similarity	NPC67158
0.7079	Intermediate Similarity	NPC30102
0.7079	Intermediate Similarity	NPC128816

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 NPC116320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	475
0.1-0.2	3736
0.2-0.3	3272
0.3-0.4	997
0.4-0.5	444
0.5-0.6	210
0.6-0.7	15
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD371	Approved
0.7079	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3669	Approved
0.68	Remote Similarity	NPD1700	Approved
0.6705	Remote Similarity	NPD6115	Approved
0.6705	Remote Similarity	NPD6118	Approved
0.6705	Remote Similarity	NPD6114	Approved
0.6705	Remote Similarity	NPD6697	Approved
0.6591	Remote Similarity	NPD6116	Phase 1
0.6571	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6117	Approved
0.6449	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8171	Discontinued
0.6353	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7909	Approved
0.6311	Remote Similarity	NPD5344	Discontinued
0.6304	Remote Similarity	NPD1779	Approved
0.6304	Remote Similarity	NPD1780	Approved
0.6273	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1810	Approved
0.625	Remote Similarity	NPD1811	Approved
0.6168	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD8034	Phase 2
0.6162	Remote Similarity	NPD8035	Phase 2
0.6092	Remote Similarity	NPD2686	Approved
0.6092	Remote Similarity	NPD2687	Approved
0.6092	Remote Similarity	NPD2254	Approved
0.6058	Remote Similarity	NPD6648	Approved
0.6034	Remote Similarity	NPD6921	Approved
0.6022	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD3703	Phase 2
0.6	Remote Similarity	NPD3702	Approved
0.5965	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4225	Approved
0.5962	Remote Similarity	NPD7638	Approved
0.5913	Remote Similarity	NPD7328	Approved
0.5913	Remote Similarity	NPD7327	Approved
0.5905	Remote Similarity	NPD7640	Approved
0.5905	Remote Similarity	NPD7639	Approved
0.5897	Remote Similarity	NPD8296	Approved
0.5897	Remote Similarity	NPD8335	Approved
0.5897	Remote Similarity	NPD8378	Approved
0.5897	Remote Similarity	NPD8380	Approved
0.5897	Remote Similarity	NPD8379	Approved
0.5893	Remote Similarity	NPD8297	Approved
0.5843	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5777	Approved
0.5823	Remote Similarity	NPD3728	Approved
0.5823	Remote Similarity	NPD3730	Approved
0.5818	Remote Similarity	NPD6686	Approved
0.5812	Remote Similarity	NPD8294	Approved
0.5812	Remote Similarity	NPD6319	Approved
0.5812	Remote Similarity	NPD8377	Approved
0.5806	Remote Similarity	NPD4238	Approved
0.5806	Remote Similarity	NPD4802	Phase 2
0.5795	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7632	Discontinued
0.5763	Remote Similarity	NPD8033	Approved
0.5743	Remote Similarity	NPD46	Approved
0.5743	Remote Similarity	NPD3168	Discontinued
0.5743	Remote Similarity	NPD7838	Discovery
0.5743	Remote Similarity	NPD6698	Approved
0.5739	Remote Similarity	NPD6940	Discontinued
0.5728	Remote Similarity	NPD7748	Approved
0.5727	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD4632	Approved
0.5702	Remote Similarity	NPD7507	Approved
0.5698	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7319	Approved
0.5686	Remote Similarity	NPD7983	Approved
0.5682	Remote Similarity	NPD5360	Phase 3
0.5682	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD229	Approved
0.5667	Remote Similarity	NPD8328	Phase 3
0.5667	Remote Similarity	NPD6081	Approved
0.5663	Remote Similarity	NPD3198	Approved
0.5656	Remote Similarity	NPD8293	Discontinued
0.5648	Remote Similarity	NPD8139	Approved
0.5648	Remote Similarity	NPD8083	Approved
0.5648	Remote Similarity	NPD8082	Approved
0.5648	Remote Similarity	NPD8086	Approved
0.5648	Remote Similarity	NPD8085	Approved
0.5648	Remote Similarity	NPD8138	Approved
0.5648	Remote Similarity	NPD8084	Approved
0.5636	Remote Similarity	NPD6675	Approved
0.5636	Remote Similarity	NPD5739	Approved
0.5636	Remote Similarity	NPD7128	Approved
0.5636	Remote Similarity	NPD6402	Approved
0.5632	Remote Similarity	NPD4224	Phase 2
0.5631	Remote Similarity	NPD6399	Phase 3
0.563	Remote Similarity	NPD8516	Approved
0.563	Remote Similarity	NPD8517	Approved
0.563	Remote Similarity	NPD8515	Approved
0.563	Remote Similarity	NPD8513	Phase 3
0.5625	Remote Similarity	NPD6372	Approved
0.5625	Remote Similarity	NPD6373	Approved
0.562	Remote Similarity	NPD7492	Approved
0.561	Remote Similarity	NPD7736	Approved
0.5607	Remote Similarity	NPD8418	Phase 2
0.56	Remote Similarity	NPD386	Approved
0.56	Remote Similarity	NPD388	Approved
0.56	Remote Similarity	NPD7524	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